I asked her what a Saturday felt like back then.

“The same as a Tuesday,” she said. “Nobody understands that unless they’ve lived it.”

8 years of this.

Undergrad, then graduate school, then a year in France that was supposed to be the reward at the end of all that discipline. And somewhere on the other side of it, she had to answer a question that never left her mind.

What do you actually do with a life that was built entirely around six hours in a room?

Touching some grass

She found her first answer at a toy company, kinda cute. International content producer, using the languages she’d picked up in France and the music technology skills nobody else in the building had.

“It was a kind of unicorn job because it was creative and stable, which rarely happens.”

But that was 35 hours a week in a cubicle, after a decade of practice rooms that at least had music. Her friends saw it on her before she said anything. They kept sending her job postings until she finally snapped.

“If I leave this job, it will not be to walk into another office.”

A lil math and no rage-quitting were the next steps. Her employer matched contributions to her 401 (k), the retirement account most American companies offer, and the money would actually be hers to keep for three more years. That gave her permission to stop panicking.

“It gave me the time and space to find the next right thing,” she said, “instead of leaving before I knew what I was leaving for.”

So she used the three years. Horticulture classes at a local botanic garden after work and volunteering at parks on weekends quietly building a second life alongside the one that was paying her bills. She told almost nobody until it was real enough to say out loud.

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She found her thing

The moment happened in her own front yard, and there was nothing cinematic about it. She was on her knees in the dirt on a weekend afternoon, doing the kind of work most people would call a chore, and it hit her that these were the best hours of her entire week. It became a simple fact she couldn’t argue her way out of once she’d noticed it.

“It felt nice moving toward something I actually loved instead of running from something I didn’t.”

What came after took nerve. The same nerve that it takes to quit something that is working but you know it isn’t you or isn’t right for you because you don’t know what’s next.

An eight-month paid internship, a real pay cut, no promise of a job waiting on the other side. Horticulture doesn’t come with the safety net of a corporate ladder. It’s seasonal, sometimes six months of work and nothing guaranteed after. She and her boyfriend at the time (her husband) sat down together for the logistics conversation. How long without good insurance? What would it cost to bridge the gap themselves? They planned for almost everything, she admitted, except the possibility that the next job after the internship might not offer insurance either. It never came to that. But if it had, she said, they’d have figured it out the same way they figured out everything else. Together, with a spreadsheet between them.

The internship led to a full-time position at a private estate. From there, years at a public park that eight million people pass through every year.

Age forcing the circumstances.

Ten miles of walking on most days, kneeling, crouching, crawling, hauling fifty-pound buckets of soil across acres of ground, for years.

“Fifty pounds of soil feels very different at thirty than it does at fifty.”

That change was what pushed her out of the job she misses to this day.

She’d moved into management for the last two years there, mostly because the pay in her city didn’t move much unless the title did. She loved the garden. She loved the people who tended it alongside her. She did not love managing a public park from behind a desk she never wanted.

A year or so later, a director position opened, and colleagues told her to apply, so she did. She was doing parts of that job unofficially for close to a year and a half already. She didn’t get it. That alone might not have ended anything. What ended it came after. She asked for feedback after the process. Anything that might help her understand and grow. But whoever she asked would pass her around like a baton until she realised she was not going to get any answers because there were none.

“I was sick of being the only adult in the room,” she said. “After 7 years, you’re owed feedback. They didn’t owe me the job. They owed me that.”

There was also practicality here. Horticulture is a small world, especially in one city, and staying in it might mean staying small forever, or eventually uprooting her whole life to chase the next opening somewhere else. She wanted her kind of freedom. That wanting, plus a silence she never got an answer to, is what finally turned her toward code.

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Back to not touching grass

Taryn taught herself enough programming, on the side, around a full-time job, to get accepted into a coding bootcamp. The same instinct that got her out of the toy company, applied to an entirely different door. The bootcamp was hard, she admitted, but what followed was harder.

Five months of searching and 400 applications. All of it happening while COVID had her classified as an essential worker, carrying exhaustion that had nothing to do with job hunting and everything to do with getting through a strange, frightening year.

“You can’t control how many interviews you get, or how many people respond. You can only control the hours you put in. Set your goals around anything else, and you’re just signing up to be disappointed.”

She landed the job she has now, a developer at a charter school management organisation. She doesn’t love it the way she loved the garden, and she said so without flinching. But she likes it and finds real interest in solving problems that help teachers reach more students. And she found something in it she hadn’t expected. Maintaining an existing codebase, she said, isn’t so different from tending a garden that was already planted before you got there. You’re not starting from nothing either time. You’re removing what doesn’t belong, adding what does, keeping something alive that existed long before you and will exist after you leave.

I like that analogy.

Behind the scenes

There is a part of this story that sits underneath everything else, and Taryn didn’t hide it; she didn’t dwell on it either. She’s lived with clinical depression since she was around twelve years old, though the official diagnosis didn’t arrive until a few years ago. There was a lot of family baggage she was carrying. Her friends and her brother were her support system, and she is truly grateful for them.

Music got her out of that house. It paid for school. It gave her twelve years of discipline, somewhere to live when nowhere else would hold her.

Near the end of our call, I asked her something lighter, almost as an afterthought. If she had to pick only one to return to, music or gardening, which would it be?

Her answer came way too fast.

“It would be gardening. I didn’t really pick music for myself. My parents picked it for me. Gardening is the first thing I ever actually chose.”

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Her days now

These days she takes a ferry to work most mornings, reads on the ride in, drinks her coffee slow because there’s nowhere to rush to. She bikes home when the weather lets her. She disappears into a dance class instead of eating at her desk on some days. None of it changes the forty-hour week. It just makes the week feel like it belongs to her a little more than it used to.

“It takes energy,” Taryn said. “You’re already tired from the day, and then you’re deciding if you have anything left for a class after. But if you skip it, all you have is work. So you have to have other things.”

She doesn’t believe in mapping out the next 30 years. What worked for her was this: pick something you can commit to for five or ten. Learn everything the role has to teach you while you’re in it. Be kind to the people around you, since she still counts close friends from every single job she’s ever held. And build a life with more in it than the job, because the job will end someday and the rest is what you’ll actually have left.

Thank you for reading! If this resonated, share it with someone who’s figuring it out too :)

By the end of the call, I understood why.

The denied potential

Rachel had multiple scholarships and a real shot at a music conservatory. She had the talent that gets noticed early. But at 17, she got pregnant, and by the time she sat across from the dean of the music department, she was already an undeclared major, basically asking for permission to still exist in the world of music.

He indirectly told her no. He told her she didn’t have time to practice piano seriously anymore, while somehow still expecting her to take guitar lessons, join the choir, and sit through his own piano lessons on top of all that because “she could play everything that he will never be able to.” Besides the talent, Rachel was also gifted with hands that could reach 12 to 13 keys.

“You want me to do all this extra stuff, but you’re saying because I have a child, I can’t be a concert pianist,” she remembers thinking.

She was done with him in that moment.

Done with him but not the piano. There was a second attempt years later, a shot at Carnegie Hall this time. A teacher told her to sit up straight and still, which, given her hypermobility, was as if asking gravity to behave differently. She calls the involuntary wobble the Elvis knee at the piano.

“I’m glad I’m not paid to do it because I would have gotten burnt out.”

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Pivot 1: 20 years with just a word

At 19, a small epiphany arrived while she sat in her parents’ living room. There was no warning.

“What am I going to do with my life?”

“Weddings.”

She was speaking to herself at that point. The word just landed with no context. She did not have any relatives in the industry, nor did she attend a recent wedding.

“It just hit me”, she said. “There was no influence to it whatsoever.”

That was the origin story of her career over the next 20 years in the form of bridal shops, florists, catering, and event management. Here I was, waiting for her to give me a reason, even in retrospect, but she never did. It was just that word. Weddings.

Pivot 2: Grief, in the shape of a push-up

Her father died suddenly of a heart attack in April of 2008. She’d already started training with a friend before he passed, and watching him go so fast entirely rearranged her thinking.

“I got to keep going,” she told me, “because hopefully I got to make it longer than he did.”

Her friend, meanwhile, kept noticing small things Rachel would casually mention mid-workout. Things like tricks about form, how shifting your shoulders changes a push-up, etc.

“You should be a personal trainer”, she told Rachel.

So a few months into grieving, that’s exactly what she became, and she started a Doctor of Physical Therapy program part-time alongside it. Money was tight, and her son’s father wasn’t around, so she stitched together whatever paid. Personal training, piano lessons taught door-to-door at other people’s houses and bookkeeping for her father before he died- 15 minutes a week for $150, which she took without hesitation.

“I get bored, apparently,” she said, “but everyone’s always seen me as a little bit unconventional. It’s fine.”

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Pivot 3: 18 months, and a laptop full of grocery receipts

Then her knee gave out. A fall turned into 18 months of unreliable walking. Doctors ran MRIs but found nothing definitive, so they told her she was probably fine and gave her a diagnosis that never stuck. Other days, putting weight on that leg was impossible. She’d have to drag it behind her with no crutches yet.

Bored out of her mind and unable to drive safely, she found a strange, small way to keep some money coming in. Amazon’s Mechanical Turk platform, doing tiny paid tasks online, in her case transcribing grocery store receipts, earning 5-25 cents apiece.

“At least it’s something,” she said. “I had free paper towels and toilet paper for the month.”

She knew it wasn’t glamorous work, but there’s no moment in her entire story, across every single arc, where Rachel describes giving up as an option she seriously considered. When I pointed that out to her directly, she laughed and admitted she’s probably just good at masking it.

“If you start to ruminate on things, you’re never going to get anything done,” she said. “Stop and go do it. Stop and do five push-ups and call it good, if that’s where you’re at in your day.”

A casual way to drop life philosophy and a personal attack. I can’t do a single push-up lol.

Pivot 4: $35 per week to six figures a month

Eventually, her surgeon gave her a verdict. No lifting over fifty pounds. No standing or sitting more than two hours at a stretch. There was no specialist around to refer her to either.

Basically, a “Good luck finding a job.”

So she built her own job. A cleaning business, because cleaning let her move constantly without carrying anything heavy, crouching and kneeling instead of standing or sitting all day- a great passive workout. Her first client was her husband’s best friend’s bachelor pad. Living room, kitchen, main bathroom, $35 a week, using whatever supplies they already had lying around.

She told new clients upfront that she had no LLC yet, no insurance, just her. They paid her anyway. Word of mouth built the rest. There was no advertising budget, no Google ads, just referrals and an old listing site called Thumbtack.

Three years later, she was grossing between $70,000 and $100,000 a month.

She eventually sold the company to her manager for far less than the revenue might suggest, since a service business like hers is mostly a client list wearing a company name. Lose the client list, and you lose the business.

“I can do it again” was her mentality.

She had the next thing already loading.

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Pivot 5: A bluff about China’s GDP

Somewhere in the middle of all this, her marriage ended, for reasons more serious than she’d expected when she went looking for the truth behind it.

She sold the cleaning company not long after. Moved 90 miles into the countryside for a new relationship, taking a listing off Indeed for something called a house manager position. Her ex thought it sounded like a scam. It turned out to be a butler role for a billionaire’s vacation estate, and the screening process included the Watson-Glaser test, the same critical reasoning exam typically used on attorneys. She hadn’t prepared for any of it. One question asked her to reason through decades of Chinese GDP growth. She had no idea but improvised an answer anyway.

She scored well and chalks it up to luck.

The in-person interview went even worse, she claims. The principal told her directly that he didn’t like hiring people who ran their own businesses on the side. She flew home certain she’d blown it completely. Weeks of silence followed. Eventually she emailed, thanked him for the chance to meet, mentioned she was in the process of selling her company, and said if he still needed a butler, she’d love to talk.

Two hours later, she had the job.

“I’m secretly taking notes,” she told me, describing the mindset she picked up just from being near someone who’d built serious wealth from very little. He’d be up most mornings before six, retired, in his seventies, answering emails because he wanted to.

“It’s all about your mindset,” she told me. “It has nothing to do with how smart you are. It’s, I’m going to keep doing this no matter what, and I’m committed to it.”

A year after she left, she emailed him once more to say thank you. He wrote back that he’d known all along she’d manage fine on her own.

She was, in her words, just shocked he’d bothered to reply at all.

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Pivot 6: The travel agency, built in secret

While still working as the butler, Rachel started booking travel on the side, in secret, without telling her boyfriend or his friends. She’d already learned what that circle thought of self-employment. Crabs in a bucket, she called it. People who’d criticise her for not having a steady paycheck while also mocking her for trying to build something of her own.

For nearly a year she kept it entirely to herself. Then word got out. Friends of her boyfriend would call asking how to book a swim-with-pigs excursion in the Bahamas, take the help, never book with her directly, then thank a stranger at a party months later for planning their honeymoon instead.

By early 2020, she had enough bookings to quit the butler job. She was about to double her income doing something she’d built from nothing.

Then the world shut down.

The same week she lost the butler job to COVID uncertainty, every travel booking she’d built- roughly $70,000 in potential commissions- disappeared in just a few days. Nobody could travel anywhere. She spent months on hold with suppliers, filing for unemployment, watching her claim get lost in a system so overwhelmed it took three months to acknowledge she existed in it.

She applied to hundreds of jobs that summer. The best offer she found was $14 an hour, 90 minutes each way by car, for a job she was significantly overqualified for.

This is giving 2026 job market..

“I laughed at them,” she said.

Instead, she filed her own LLC and went out entirely on her own.

By 2023, she was ranked among the top 25 group travel specialists in the world, 6th worldwide with one specific resort brand, and has taken home top 1% sales awards ever since.

Now comes my fav detail in the story

Not long after her relationship ended, one of her partner companies called to check if she was upset with them. They’d mailed an award to her old address out of habit. Her ex had written Return to Sender across it, in what the delivery driver apparently described as a fairly furious hand.

The awards kept finding their way back to her at her new address, once someone finally updated the file.

The reframe that changed how the awards feel

Near the end of the call, I asked whether owning all of this ever got tangled up with who she is as a person.

“Yes, and dangerous if you’re not careful about it,” she said immediately.

A single unkind comment online starts to feel like a verdict on YOU, not your business. She’s watched it paralyse other travel advisors she now mentors, people too scared to post because a stranger might say something in the comments.

She had to build a different frame for herself over time. She’s not the owner but a steward of something handed to her, the responsibility to keep tending it well.

“When I get those awards now,” she said, “I don’t feel special about them. This is just what I get for taking care of this thing.”

These days her business runs on automations and boundaries she built the hard way. An email signature that reads “all calls by appointment only”, a separate line reserved only for clients mid-trip. She still keeps two businesses running and mentors other advisors on the side, coaching that started as a course and turned into something closer to a real relationship. Revenue has dropped since she pivoted travel niches recently. She says that part doesn’t worry her, and I don’t doubt her one bit.

Thank you for reading! If this resonated, share it with someone who’s figuring it out too :)

That’s the line a choral director gave Sonia when she was applying to college, thinking about a music program.

“If you can imagine yourself doing something else, don’t do music,” he told her. “It’s going to take everything out of you.”

She sat with that and thought, “honestly, I probably could do something else.”

So she didn’t go into music. She studied international business and computer science instead. It sounds like advice that closed a door but, surprise surprise, it didn’t. It just meant the door stayed shut for about fifteen years, and when it finally opened again, it wasn’t a plan. It was a wedding.

But we’ll get there.

The studio next to the college

Before business and before any of it, Sonia wanted to be a singer. She told her mom this as a kid, the way kids do, and her mom said maybe think about something else. She wasn’t wrong. Sonia wasn’t good enough to be a singer, and she’ll say that herself now, no bitterness in it.

At fourteen she found dancing instead. Salsa, Latin and ballroom dancing. She fell into it like she found her thing, the one thing she’d do if she knew she’d die tomorrow. By the end of high school, she wanted to take a year off before college to do it full time. Her parents said no, worried and rightly so, that a year off would become permanent.

So they compromised and picked a college close enough to her dance studio so she could keep training while she studied business. It’s a small detail, but it tells you something. Nobody around Sonia ever said stop. They just kept building slightly smaller boxes for the same thing to live in.

The 5 pm feeling

After college, she tried the business route seriously. A year in Belgium doing economic research for a nonprofit. Then public relations back in the US.

She hated it.

Every day at the office she’d dream about the studio like her mind and body were still there.

She wasn’t doing well at the job either, because of it. HR eventually called her in. Quit or be fired, more or less. So she quit.

She moved to New York and tried again to land something in business, because that’s what her degree was for. Every interview was the same feeling of nothing. Eventually, she just needed a job. She walked into a dance studio with nothing but ten years of experience and a request.

“Can I have a job?”

The owner said her first class was that night.

Things just somehow click when we have nothing more to lose…

That’s how her professional dancing career started without a plan.

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A week before grad school

While all of this unemployment and studio-hopping was happening, Sonia had also applied to grad school, because she needed to be doing something with her life and it seemed like a reasonable next move. She got into Rutgers for a Master’s in social work. Housing was arranged, internship lined up, and she was a week away from her first class.

And she pulled out.

“I can always go back to grad school,” she told me. “I can’t always dance.”

That’s it. That’s the whole reasoning. No dramatic turning point, just very simple math about which windows in life close and which ones don’t.

She moved back to Boston, ran a dance studio, competed with a professional partner. At their peak, they were ranked 32nd in the country. She was around 27, getting old for the sport, and starting to think about life after dancing.

Two buckets, one airport

Sonia describes her life at that point as two buckets. One bucket was dancing, winning, training, and everything dance. The other bucket was everything else not dance. Retirement savings, friends, dating. A part of adulthood that wasn’t happening because the first bucket had taken up all the room for over a decade.

She woke up one morning and the second bucket looked more attractive than it had in years.

They were mid-tour, five competitions in six weeks, sitting in Chicago’s airport. She looked at her partner, sighed, and said, “I’m done. I can’t do this anymore.”

He was four years younger, still had time left in his body for the sport. But he got it. “Okay,” he said. “We’re done.”

There was no blow up or a fiery argument. It was just an understanding that she had sacrificed it all for the last ten years and had nothing left to give.

She flew home.

That was the ending of a decade-long career.

What she didn’t say out loud for years

I want to mention something Sonia told me in passing. Her sister, two years older, went into tech. Sonia watched her work maybe a tenth as hard and end up with a hundred times the money. Three houses, two kids, and all that stuff.

“That was really hard to see,” she said. “I was working my ass off and could barely make ends meet.”

Every career Sonia built, she built starting over from level one, while her peers kept climbing the same ladder. That’s a cost that doesn’t show. It just sits there, party after party, for years.

The introvert she found during a pandemic

After dancing, Sonia did a stretch of business roles to re-enter corporate life. A coworking company, sales, HR and community work. Then her sister got married in California, so Sonia moved out, took a job as an admin assistant for a tech company, and for the first time in her adult life, clocked out at 5 pm and went home to a life that was hers to do what she wished to do with, at that moment.

Then the pandemic hit, and she lost the job.

“That was awesome,” she said, and she meant it. Unemployment assistance meant money, and no job she hated meant peace. And in that quiet, she learned something about herself that surprised her: she’s an introvert. After years of teaching dance all day and helping people all day as an assistant, coming home exhausted every night, she finally had days with no one in them, and she loved it.

When she had to work again, she landed in an operations and HR hybrid role, discovered she was actually good at it, got her HR certification, and eventually moved into the job she has now. Head of HR at a biotech company. She started three years ago at a fairly junior HR title. Her boss left a couple of months ago, and now she runs it.

The wedding that opened the door back up

Five years after retiring from dancing professionally, Sonia’s itch for creativity came back. She had played harp long before she started dancing, but decided to trade the strings for dance shoes as a teenager. Now that she wasn’t spending all of her time in the dance studio, Sonia could return to playing music. She put up a couple of videos on Instagram.

psst, it is linked below

A stranger messaged her. Would she play a wedding?

She said probably, sure.

It snowballed almost immediately. That one wedding turned into every other weekend booked with weddings, corporate events, and gigs. She has a website now too. Solo shows. A seat in an orchestra. A stable nine-to-five during the week, and creative work she can turn up or down depending on how the month at the office is going.

Fifteen years after a choral director told her only pursue music if nothing else will do, she’s doing both. The wait because it took her that long to build a life sturdy enough to hold the thing that couldn’t be a career on its own for her.

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Her template

I asked Sonia what got her through the hardest, messiest stretches, and her answer was practical to the point of being funny.

Therapy, she said first. Lots of it. And then a set of rules she’s built for herself over the years.

One: do hard things on purpose, because your capacity for hard things grows every time you do one. It’s ok to be scared. It’s ok if things don’t work out the way you planned (in fact, they probably won’t). Take your fear and step through the ring of fire with it. Confidence doesn’t come before you do the scary thing. It comes after. She compared it to a ditch you keep falling into. First time, you don’t see it coming. Then you see it and still fall in. Then you fall in from the side because it looked different there. Eventually you walk around it clean. That’s the whole process, repeated on every hard decision she’s ever made.

Two: listen to yourself and your body. Humans really good at using our brains to convince ourselves we should do the “correct” thing. Our bodies always tell the truth. We can have two opposing feelings at the same time. You can be scared and do the thing that scares you. You can love someone and they aren’t the right person for you. Being able to hold that duality really helped her navigate hard situations.

Three, and this one made me laugh, a friend of hers wanted a two hundred dollar backpack he couldn’t afford and told her he deserved it anyway. “I’m like, Tim, if I don’t have the two hundred dollars, I don’t have the two hundred dollars,” she said. No negotiation with herself about deserving things she can’t pay for. The idea is less about depriving yourself of things you want, rather a practical consideration.

“Being kind to myself now (not spending money I don’t have) so that I can set myself up for success in the future (not have financial debt).”

Four: Things don’t happen just because you want them to, no matter how badly. Building a company, making the Olympic team, or becoming a great parent, takes deliberate work. Drive matters, but how you direct that drive matters just as much. How do you practice your craft? How do you prioritize your time, money, relationships, and energy? What are you willing to sacrifice to get to your goals?

Small rules she’s used to make some of the biggest calls of her life.

Deprioritising on purpose

Sonia is 38 now. She used to believe, like a lot of people do, that certain things had to happen before 30. Married, kids, all of it. Thirty came and went, and she didn’t combust.

She did ask a better question, though. Where is this pressure coming from? Is it real or perceived? If it’s about wanting kids, fine, then what am I willing to sacrifice for that, and what am I not?

Her current answer: she’s deprioritising marriage and kids, because they’re not what she’s structuring her life around right now. What she’s structuring around is this: save aggressively, retire early, become a full-time harpist, keep selling the bread she bakes on the side.

“It would be a hell of a lot easier if I didn’t have a job,” she told me. “So I’m going to keep kids out of the equation.”

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What it cost

I asked what she’d tell people about the sacrifices behind all of this, and she didn’t romanticise a single part of it.

She missed graduations. She missed big family events. She lived paycheck to paycheck through most of her dancing years, sitting at dinner with friends who all ordered food while she didn’t, because she needed that ten dollars for an entry fee instead.

“It’s not only about working hard,” she said. “It’s about saying no to finding a partner, having children, having a life that looks like everyone else’s, so that you can have the thing YOU want.”

She doesn’t call any of it a straight line, and she’s not interested in pretending it was one. Five careers, starting from level one every single time, watching her sister’s life get easier while hers got harder for years before it evened out. But every version of Sonia along the way, the dancer, the admin assistant, the HR specialist, the harpist, was chasing the same instinct. Find the thing that feels right, keep moving toward it, and be honest with yourself about what you’re willing to do to get there.

Thank you for reading! If this resonated, share it with someone who’s figuring it out too :)

Disclaimer: this issue has no subject except me, which is a little embarrassing to write.

A few weeks ago, a master’s student named Carli messaged me after finding The ZigZag on Reddit. She is from Peru, studying at the Harvard School of Engineering, and she was spending her summer trying to understand career pivots and the difficulty of it as a systemic problem worth solving. She wanted to talk to people who were close to the problem.

She wanted to talk to me.

If I had to be honest about what that felt like, I’d say flattered, obviously, but also confused. Because I am not the person with the answers here. I am the person writing about people with the answers. There is a difference.

I said yes anyway, and I went in with nothing prepared because I had no idea what to expect.

What I didn’t expect

The response when The ZigZag first appeared on Reddit was not something I had planned for. Comments, messages, people wanting to share their stories, people saying they had been looking for something like this. I was not prepared for any of it, a lil bit overwhelming too (in the best way). 10+ issues later, a Harvard student was asking me to explain what I had learned.

So, I showed up and just spoke.

The surprising part was this: the words came out like an artist’s strokes on a painting, which I had not planned. I started answering Carli’s questions and found myself saying things I did not know I thought. To clarify, I wasn’t making things up. I realised I was saying things that had been sitting in me, collected slowly across every conversation I had done for this newsletter, and I had never had a reason to put them together until someone asked.

She did ask some great questions.

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The starting line

Carli asked me where people get stuck. And I said, “The start”, without a second thought.

Most would think it is the middle of the transition or the leap itself, but it’s before any of that. The moment where you are entirely in your head, running scenarios, calculating every possible way it could go wrong, including the absurd ones, waiting for some sign that it is safe to begin. Most people spend the longest here.

And then I said something I had not said out loud before. The fight people think is with the job market, or with finances, or with their family’s expectations, is almost always, underneath all of that, a fight with themselves first.

All the external conditions are real. Financial pressure, societal messaging and other responsibilities are real. I have spoken to Nina who grew up in a post-war country being told that girls are not built for logic. I have spoken to people who were the sole income for their families and could not afford the luxury of uncertainty. I have spoken to people whose entire support system believed in the straight-line path and could not understand why anyone would want to leave it. All of that is real, and all of it weighs on people.

But alongside all of that sits an internal conversation that most people are having completely alone and in silence because they think they are the only one having it.

That is why the stories matter. Motivation or proof that the leap is survivable is one thing. But when someone reads about another person’s internal fight that is never talked about publicly, they realise nothing is wrong with them. It is just the thing that everyone goes through when they want to change direction and do not yet know if they are allowed to.

“Most of us are looking for permission, and we don’t even realise it” – a Substack note I read a while ago, which is so true and also the reason I use the word “allow”.

What I keep noticing about women

Carli asked me who The ZigZag spoke to most. And I found myself talking about women for a long time.

Men and women alike zigzag. But women who reach out are often carrying more variables at once. To name a few, financial independence that was never fully theirs to begin with. Children who need childcare while their mother studies for something that might eventually give them all a better life. The guilt of that choice, which is real and nobody warned them would sit so heavily alongside everything else.

The juggle, as one person put it to me recently, is real and it hardly ever feels graceful.

Then Carli said something that got me thinking. She had noticed that when women consider a career transition, they tend to look at what they will lose first. It could be money, ground, credibility, time or something else. When men consider the same transition, they tend to frame it as something they will gain. A better role, more money, a new set of experiences. It’s the perspective difference.

I just sat with it because it maps so cleanly onto so many conversations I have had for this newsletter, and I had never seen it framed that way before.

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The LinkedIn problem

Carli asked me whether LinkedIn was a useful space for the kind of conversations The ZigZag was trying to have.

I was more honest than I expected to be.

LinkedIn is a place where people go to talk about success, where careers are presented in their polished versions, where the professional self is always in good lighting. It is not naturally a place for the unfiltered version. The actual content of this newsletter is raw, and the stories are honest. But the way I introduce them on LinkedIn has to meet people where they are, which is somewhere between inspired and aspirational.

Reddit or Substack is different. Those are places where people write honestly because they want to. And that gap between the platforms where honesty is welcome and the ones where it isn’t so much is part of why these stories feel so rare. They exist but perhaps not as accessible.

Your judgment is the currency.

At some point, I was talking about portfolio careers. The idea that a non-linear path is an asset and not a liability as most would assume. The person who has moved through biology and operations, or music and coding, or architecture and consulting, is not scattered. They are equipped to connect dots that a specialist cannot see. They carry judgment that only comes from having lived in more than one world.

And with AI making knowledge more accessible than it has ever been before today, judgment becomes hardest to replace. Before it was an assessment of how much you knew, but now, how you weigh what you know becomes just as important. How you read a situation that does not fit a template. How you make a call when the information is incomplete.

That is what a non-linear career builds, often without you realising it is happening.

Carli had also raised something that I found interesting. She had noticed that people often wanted to speak to someone who had actually walked a similar path, rather than a career professional who had studied it from the outside. The trust was different, and I think this is connected to the judgment point. What people are really looking for is not just information but also calibrated experience. And that only comes from having made the call yourself and lived with what came after.

This is, I think, why the people who I’ve spoken to for The ZigZag are believed in the way that they are. They are not telling you what to do. They are showing you that they did it, and what it actually cost, and what happened on the other side.

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What running this has taught me.

I came out of that conversation more surprised than I went in.

I had been collecting things without registering that I was collecting them. Every interview had left something behind. Some small understanding of what it actually costs to change direction, what the internal fight feels like up close, what the variables are that make it easier or harder for different people in different circumstances. And I had not known I had any of it until someone asked me to explain it.

I think this is what 10+ issues of The ZigZag have taught me, slowly and without announcement, things I did not know I was learning.

Thank you for being the reason I had something to say.

Carli, a special thanks to you for asking these wonderful questions. They allowed me to structure all the thoughts and conversations.

Thank you for reading! If this resonated, share it with someone who’s figuring it out too :)
If you know someone whose story deserves to be told, I would love to hear about them.

Tatjana’s first proper hospitality job was inside a converted Gothic cathedral. A privately owned boutique hotel, stone arches, and just the beautiful architecture you’d imagine.

“I felt really lucky to be working there,” she told me. “It was one of the first jobs where it felt special.”

But before I could finish clearing the beautiful gothic cathedral I’d imagined in my head and pay attention to her story, she mentioned something else that snapped my attention back. Legal insurance. She’d taken it out early in her hospitality career on a friend’s advice, not expecting to ever use it. Bless that friend because she used it three times. Twice because the industry, her words, notoriously doesn’t pay you on time. The third time because she was still on probation at a job, told her employer she was pregnant, and was let go before probation ended.

The insurance meant her old employer had to keep paying her full salary until she moved into maternity leave. That’s the whole industry in a sentence from Tatjana’s experience. The buildings are beautiful, but the protections are not.

The game he wouldn’t pause

She moved to the UK to be with her partner and they had two kids. And when COVID happened hospitality with a young family, she said, felt completely incompatible, so she drifted through part time cafe and pub jobs while something underneath her kept building up.

It was not a big fight that broke her. It was asking her partner to handle the kids when they woke up crying and hearing him say “just after this game” while she sat there unable to concentrate on anything, unable to leave them, unable to wait fifteen minutes for someone to pause a PlayStation match.

“I had quite a few times I was just either really angry or crying,” she said, “getting them back to sleep, then turning off the laptop and just going to bed.”

She was financially dependent on him at the time. Her mother paid for their youngest’s childcare because Tatjana’s family didn’t qualify for free hours, her ex earned too much on paper for that, while in practice the money never quite stretched the way it should have.

“I knew I couldn’t keep doing this forever,” she told me. “I know I’m clever. But it can’t be it.”

It wasn’t one dramatic event but the accumulation of small moments like this one, the sense of carrying almost everything herself, and the decision that she was done waiting and ready to create the opportunities for herself.

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What was already there

Tatjana had tried coding before, in the bare minimum time she’d have to steal from her day while taking care of a baby. Her now-ex, a software engineer, kept telling her she’d pick it up naturally, given how many languages she already spoke. She never really took it to practice, until an epiphany, if I can call it that.

What moved her was a psychedelic experience, arranged with a shaman, something she’d read about carefully beforehand because it was too late to now say no to this after she’d already said yes to a friend. She was nervous, given she had two children and a healthy amount of caution about doing something “silly and reckless.” In short, doing it for the plot.

I did not see it coming either.

She wasn’t seeing things like you’d imagine. No visions but seeing things within herself more clearly. A fear she hadn’t fully clocked was running her decisions, the fear of not being good enough. The experience handed her the sense of agency and urgency to finally act on the decision that had been sitting there all along with the courage she already had.

There is no time to waste.

“I can think about it and wonder, without ever sending out an application,” she told me. “I was like, okay, what’s the worst that can happen? I’m still in the same position I am now.”

She found a European startup running an online coding programme, flexible hours, no fixed nine to five, built for people who have lives besides work. Scholarships were available if you had a European passport which she did, from ten years earlier, and hadn’t thought of it as an asset until that exact moment.

She got in.

The text box that could crash your app

Once enrolled, Tatjana went looking for a mentor. A paid mentor was not something she could afford at that time. And this is where you get the story behind the title of this issue. She posted on Reddit, where she’d mostly been a quiet lurker in tech forums, and asked if anyone would be willing to help.

Nothing beats Reddit. I love that place for what it has to offer.

Three people reached out. One in the US fizzled out over the time difference. One in the UK stuck and is still in her life today.

She told me about a bug she brought to him once, a text input field with no character limit. “He was like, oh, you have no restriction there. Someone could literally upload War and Peace and it would just crash your app.” She hadn’t considered that.

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Fresh eyes

Tatjana landed her first tech role through a recruiter she’d followed on LinkedIn with one interview, and a job in tech support at fintech company, with a clear condition she set from day one. She wanted to become a developer, not stay in support forever.

What she liked the most here was being asked what she thought about something.

In hospitality, she said, you come out of university convinced everyone wants your opinion and get disillusioned fast when nobody does. Here, they had her walk through the entire user journey as a newcomer and document every clunky, counterintuitive moment she hit along the way. Small things nobody inside the system notices anymore because they’ve stopped seeing it.

“They really valued fresh eyes,” she said.

They gave her her own projects. By January she was splitting her week between support tickets and actual development work. The title recently changed to Junior Fullstack Developer.

The long way round, she called it. But she got there.

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The rhythm now

Her days have a shape to them now that she’s visibly proud of and puts a smile on her face. Up at six followed by gym then breakfast, lunches packed, school drop off. Desk by mid-morning, tickets first while they recruit her replacement, then development work for the rest of it. Afternoon school pickup, dinner already going in the slow cooker, homework, bedtime, stories, and by ten she’s done.

“It’s full. It’s a lot,” she said. “But it’s mine.”

The role is remote, and every few months there’s an overnight trip to London built into the job, which she described shyly, as a lovely little reset.

Near the end of our call, I asked about something she’d mentioned in passing. She’d bought a house.

I asked how it felt, standing there with the keys.

“It’s very complicated in the UK,” she said. “It just takes forever. I signed the mortgage deed. I’ll probably have the keys in three or four weeks.”

I was just a lil bummed out because I really wanted to capture her feelings onto this one. I’m still waiting on her email to tell me how it feels to finally hold the keys she truly earned.

The years it took

None of this happened in an afternoon. It happened in the space between school drop-off and pick-up, most days, for years.

A typical day during the course: up, kids ready, breakfast, drop-off, then studying until three when she had to collect them again. Then snacks, attention, dinner, housework threaded through all of it. After bedtime, she’d try to sit down again. Some nights it worked. Some nights she was too tired to open the laptop. Some nights the kids woke up and that was the studying done for the day.

“It’s difficult when you’re a parent,” she said. “You’re constantly engaged.”

There was a schedule she rebuilt every single day, whether or not the day cooperated. She always showed up.

Forgotten version of herself

Tatjana talked about how, as a child, you picture one version of yourself and assume that’s the one you’ll grow into. Nobody tells you how many times you’ll have to rebuild that person from scratch as life keeps happening to you.

“I think that’s really matching with the zigzag,” she said.

It is. She used to think a career meant picking one industry and staying in it. Looking back now, she doesn’t think there was ever a shortcut available to her, every step, the cathedral, the probation, the PlayStation nights, the retreat, the years of studying after bedtime, taught her something she still uses today. The zigzag wasn’t the detour from the path. It was, yet again, the path.

Her advice to anyone circling their own version of this: find a mentor, even an informal one, even one you meet on Reddit at eleven at night. Stay flexible about which door you walk through, since the front one isn’t always open, and the side one might fit you better anyway. And get out there and generate your own luck, because it rewards people who move, not people who wait for the moment to arrive fully formed.

If you had to take only one thing home from her story, Tatjana hopes it's this:

Rebuilding your career is possible, but it takes consistent effort. And for her, financial independence has become non-negotiable.

Thank you for reading! If this resonated, share it with someone who’s figuring it out too :)

Terry Hui was on a work trip when he got the email.

He had just spent twelve to thirteen hours preparing for a kickoff meeting with the rest of his team. Everything was booked on the company card. A new project, new energy, finally something to do after weeks on the bench. The email came at night, his name and HR in the subject line. He said he knew immediately what it was.

The call came after the kickoff. They were letting him go with a twenty-four-hour notice. Company cards cut. The flights and the hotel he had booked, the expenses he had racked up doing what they had sent him there to do, none of it would be reimbursed. He was, for all practical purposes, stranded.

He sat in his hotel room and called his girlfriend at the time.

“I got laid off,” he told her. “As we kind of expected. I just want to sit with it for a minute.”

And then he sat there with no panic, no spiral, no thoughts of what came next.

What he felt, he told me, was relief.

He had just been laid off by one of the most prestigious consulting firms in the world, was sitting alone in a hotel room in a city away from home, and the feeling that settled over him was relief.

I spent a while thinking about what it means when the worst-case scenario feels like the best thing that’s happened to you in months.

College he didn’t want to attend

To understand the hotel room, you have to go back further.

Terry grew up in the Inland Empire, Southern California, and he never wanted to go to college. To calrify, he wasn’t aimless. He had things he loved, to name a few, drawing and taekwondo. He was good at both. But the classroom never suited him. He learned differently. Sitting still and absorbing information was not how his brain worked best. In fact, he told me his childhood dream was to be an athlete.

He went anyway, out of respect for his parents.

The first few years were rough. He struggled academically. Discipline was the real issue, not intelligence, and he’s the first to say so now.

Props on the self-work, honestly. It really showed on the call that we had.

But something shifted. He put his head down. With support from family and the right people around him, he transferred from his local community college to a university and stepped into what felt like a whole new world all over again.

He didn’t know how to find internships nor did he know how to network. Everything felt unfamiliar.

Most of us have been here at least once; some are still here.

And then one afternoon, walking to class, he passed a row of business clubs tabling on campus. One of them was a professional business fraternity. He had a short conversation with one of the members. Wasn’t immediately interested. But something called him to go back and join.

He says that this was one of the biggest decisions he’s made in his life retrospectively.

The people he met there shaped who he became professionally. They gave him the vocabulary, the skills, the network he didn’t know how to build on his own.

His senior year arrived. He was still late to internship applications because he hadn’t figured out the timing. The only thing he could find was an unpaid market research internship in his final semester that was two and a half hours one way, multiple times a week with no salary, which amounted to a few lines on a resume. But he still took it.

“Gruesome, but worth it.”

Despite having only an unpaid internship to his name, he graduated and landed his first real job at one of the most prestigious firms in the world.

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The dream job

Everyone told him this was it.

The dream company, the dream role. And from the outside, it did look like a dream. He was working with companies that shape the world. Business operations, Tech consulting, and so many other “hot topics”. The work that looks very impressive in a LinkedIn bio.

But he felt nothing.

“I always knew this was never my path,” he said. “But I still chose it.”

He had worked hard for it; he’s clear about that. He hadn’t stumbled into the role. He had put his head down and earned it. But somewhere along the way, what he’d been building toward was someone else’s definition of success. A life that had been sold to him, and that he had accepted without fully questioning whether it was really his.

The golden handcuffs, he calls it. The stability, the prestige, the salary, all of it making it very difficult to imagine leaving even as none of it felt right.

The project he’d enjoyed most ran out of budget. He ended up on the bench, which, in other words, means waiting. Looking through internal portals for new projects, applying for roles that had already been filled. Time passed with a strange, hollow feeling.

He wasn’t looking for a reason to leave. He was counting the days until he would.

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Relief

When the layoff came fast and brutally. Twenty-four hours’ notice with no reimbursements and basically stranded. And the first feeling was relief.

“I felt more alive making that ridiculous commute as an unpaid intern, than I ever did in this role.”

I did not quite know what to do with this sentence when he said it.

He was describing a two-and-a-half-hour commute, no pay, bullet points on a resume as the reward. And that had made him feel more alive than a job at one of the most recognisable firms. The internship was hard, unglamorous and completely unimpressive on paper. But it was also, apparently, more him.

There is something in that worth sitting with. The things that feel hard from the outside are not always the things that cost the most inside.

Experiments

After the layoff, he tried things.

Digital marketing. Paid advertising. He helped a friend scale a home painting business by running ads that eventually made thousands. Worked with people from The Simpsons. Built AI automation tools before the space had gone fully mainstream.

He was good at all of it. None of it meant anything to him.

“If you don’t understand yourself at a foundational level,” he says now, “none of the work will mean anything.”

He kept moving and looking. Trying to find the shape of something that felt like his.

15 minutes

He met his current business partner in college, but hadn’t started working together after both had graduated. They were both trying to figure out how to serve clients in the AI automation space when a third person had entered the picture too, someone who had found success young and was now at his own crossroads. They started working together. Every day, during their sessions, this third partner would stop them.

“Guys,” he’d say. “Let’s take fifteen minutes. Let’s talk about our principles. Let’s talk about our values. Let’s make sure we’re aligned.”

Terry told me that at the time this confused him a little. There was work to be done. Why were they stopping to talk about values?

He understands now.

The concept he came back to is called the values-action gap. The idea is this: if your work and your values are chronically misaligned, you will be, over time, more unhealthy and more unhappy. Most people don’t catch this because they don’t have a clear enough picture of what they truly value in the first place. Society, family, culture, economics, all of these things shape who you are before you’ve had the chance to figure out who you want to be. And then you spend decades course-correcting, if you’re lucky enough to realise you need to.

The third partner eventually left the group. He was always interested in biotech. He told Terry and his co-founder from the beginning: this isn’t my passion, I’m here while biotech develops, and then I’ll go, and he went when the time came.

But before he did, he told them, “Don’t chase the money. Design a life that’s aligned with who you actually are.”

Terry and his co-founder sat with that for a long time. They realised they shared the same values and the same purpose. They decided to build something around them.

They Built Novii

The company is called Novii. The mission is, at its core, about what Terry calls orientation before optimisation.

He explains it like this. Most people are so focused on doing everything right, optimising everything, making life as efficient and productive as possible, that they skip a step. Do you know yourself? Probably not. And if you don’t, then everything you’re optimising toward might be somebody else’s destination.

Novii works with people who are entering or navigating what Terry calls modern adulthood. The idea, drawn from a Stanford framework called Life Design, is that you approach your own life like a designer approaches a problem. You go inward first. You understand yourself at the root. Then you start building outward from there, designing different versions of your life, three years, five years, ten years, seeing what fits.

He wants to shape the lives of people who will eventually shape our society. That’s how he puts it. And coming from someone who spent years building a life that looked like the dream from the outside, and felt like nothing from the inside, the ambition makes complete sense.

Now tell me that sounds like someone who hasn’t done the internal work. You can’t, can you?

Thank you for reading! If this resonated, share it with someone who’s figuring it out too :)

Paola was fifteen when she figured out what she wanted to do with her life.

She was watching The Interpreter, the Nicole Kidman film where a UN interpreter accidentally overhears an assassination plot. What caught Pao’s attention wasn’t the thriller part. It was the job. Someone who moves between languages for a living, who sits in rooms full of people from different countries and makes them understand each other. That, she thought, is what I want to do.

She grew up in Paraguay, speaking Spanish as her first language, then Italian at school, then English, then a little French and Portuguese along the way. Languages had always been the thing.

Pao’s quietly out here doing a Shakira.

The problem was that interpreting wasn’t a career path where she was. It simply wasn’t available. Her idea was to take a Bachelor’s degree in English language and somehow build her way up to an interpreter or something related. When she told her mum this idea, she understood that this would basically take her down the road to becoming a teacher.

Her mum said, “So you want to be a teacher? But you won’t make much money.”

One sentence. Pao absorbed it and changed direction.

I wonder how many careers have been quietly rerouted by one sentence from someone who loves you and means well.

The “rational” choice

She ended up studying Marketing instead, partly because she’d enjoyed her high school Marketing classes, partly because the teacher was funny and made her think. She graduated and got hired as a Marketing Assistant right as she was finishing her final presentation. Exciting timing.

For a while it was fine. She was learning something new. She landed a genuinely good second job. But there was a low-level dissatisfaction that never left, the kind that’s hard to name when everything looks okay from the outside. Reminds me of Ananda from Issue #004.

By 28, it had become something harder to ignore. She was burnt out and deeply unhappy, carrying things both inside and outside of work that had made the whole picture feel impossible.

She doesn’t dress this period up. It was hard and required time, not just a plan.

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Never too late to start over

At 28, she quit the Marketing job and started therapy because that’s what the situation called for. The quitting also helped figure things out.

Around the same time, almost by accident, she took a teaching job at a school. The subject she was assigned to teach was in English. She got to work with the language every day.

That’s when it shifted.

She hadn’t expected to like it. She hadn’t expected to find that working with teenagers, those loud, unpredictable, occasionally maddening humans, was actually something she was good at. She hadn’t expected to feel, for the first time in a while, like the job was contributing something real to the world rather than just to a company’s quarterly numbers.

It wasn’t the interpreter job from the movie. But it was the same thing underneath it. Languages, People, and being useful to someone who needed it.

Her therapist, watching all of this unfold, suggested she look into Psychopedagogy, which is something like Educational Psychology, the study of how people learn and what gets in the way of it. She and Pao went through the options together and weighed them up. It became clear this was the direction.

So, at 30, Pao went back to university. Her classmates were mostly in their early twenties. She sat in those classes anyway.

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Hurry up

One person didn’t make it easy.

A former coworker, someone she’d known from the Marketing days, said something to her that she still remembers almost word for word. Pao was nearly 30, had just started the new degree, was building toward something she actually believed in. And this person said to her, “You have to hurry, because you’re already 30 and nobody will hire you.”

Pao went home and never spoke to her again.

Pao is better than me fr.

What she said back, in the moment, was this: “I want to be a teacher. Nobody cares how old you are when you’re a teacher.”

She was right. She got hired.

What does satisfaction mean to you?

She teaches Language Arts to middle schoolers now. She has been doing it for a few years since finishing the Psychopedagogy degree, and most days she loves it.

“I do most days,” she said. “Although it won’t do anybody any harm to get more money for all the extra hours outside of the classroom.”

Because that’s the other thing about teaching that nobody puts in the brochure. You only get paid for the hours in the classroom. The planning, the adapting materials, the staying late to help the kid who doesn’t have a tutor and whose parents can’t afford one, none of that has a pay line next to it. She does it anyway.

She got an email recently from her coordinator and her coordinator’s boss, congratulating her on what they called her “human approach.” She told me she has trouble accepting compliments, so she set the email aside. The satisfaction that genuinely lands for her is different and more specific.

There’s a student in her class, Korean, who struggled badly last year. Frustration that came out sideways as behavioural issues because of the language barrier; it was rough. For most teachers, he was the difficult one. For Pao, he was the one worth figuring out.

This year he shows up and tells her when he hasn’t finished something. He promises to bring in the work afterwards and actually brings it. He makes jokes with her now too.

“He’s my weakness,” she told me, laughing. “I love working with him. He’s my baby.”

The greatest satisfaction, she said, isn’t the email from the boss. It’s watching a kid who was labeled the big trouble maker, start making progress and knowing that some part of that was because she stayed.

She’s not sure if she wants to be a teacher forever. No anxiety behind those words. Teaching has made her more flexible, more human, more open to what comes next, and whatever that is, it will probably involve languages, and people, and being useful to someone in a room.

Which is, when you trace it back, exactly what she wanted at fifteen.

“You might end up doing what you wanted in the beginning anyway,” she said. “It will just take you more time if you don’t follow your instincts.”

Her mum’s one sentence bought a ten-year detour. The detour brought her back. That’s the zigzag.

Thank you for reading! If this resonated, share it with someone who’s figuring it out too :)

Amy Elliott’s original plan was Harley Davidson. She was going to be a mechanical engineer who built motorcycles, and she went to college with that plan fully formed and entirely confident.

Hold this image for a second. A Mechanical engineering student, in love with motorcycles, a high school kid who was very sure of herself.

Now I will tell you what actually happened.

Three schools, four majors, five years and one degree.

And honestly? Respect.

Every time Amy switched direction, she found the major with the most overlapping math so she wouldn’t lose ground. Mechanical engineering to actuarial science to something else entirely to Computer Science, and she only added one extra year to the whole thing. Her last semester was a single one-credit science lab because of how the transfer credits fell.

To a reader, it may feel like she was lost. But what she was doing was optimising, in real time and without a roadmap. The math was always the constant, every single time.

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First Three Years

She got her first software job, which she liked. And then, gradually, somewhere around year three, she didn’t anymore.

I asked her what a bad day looked like.

“Going in knowing you’re not going to make a difference,” she said. “So why try?”

Amy was clear that this is different from burnout. Burnout, she explains, is an exhaustion thing, a need-to-physically-step-away thing. What she was describing is something quieter. It’s the dread of going somewhere where your voice doesn’t land. Where you’re doing everything right, and things still don’t move. Where you fight the same fire on a loop, and nobody changes the thing causing the fire.

She made an unusual plan this time.

She applied to nursing school, which she got into. She was almost going to go, but she was laid off.

Aftermath

This was 2009. She had a new baby. They had also just bought a house. She was the only income coming in.

She gave herself 24 hours to fall apart after that layoff.

I did not know what to make of this when she told me. It sounds almost too clean, too controlled. But the more she talked about it, the more I understood that this is just who Amy had to be in that moment. Someone who has figured out exactly how long she can afford to feel those feelings before she has to start moving.

The first day, she couldn’t see properly on the drive home. She was crying that hard. She doesn’t know how she made it back.

The second day, she put on what she calls her armour, sat down, and made a checklist.

They cancelled the internet and the cable. Then every subscription, every non-essential thing. Kept the phones, because you need a number for callbacks. When Amy needed to apply for jobs, she drove to the library or to her in-laws’ house.

And then, because 2009 had clearly decided to be the worst for her, the stove broke. Then the fridge. Then the washing machine. All of it in the same window. She tells me this, and I genuinely cannot imagine being that person, holding all of that at once, and still going to the library to send out applications.

“We made it through,” she says. And that is the highlight of it all.

Two weeks and she got a job offer. She was convinced she’d bombed the phone interview. She was trying to find a quiet corner of the house, and there was a screaming baby in the background. Lucky her, the hiring manager had kids too, so he understood.

Nursing school didn’t happen. But something else did.

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Pivot Inside The Pivot

This new job was a hybrid. Part software development, part report developer. A couple of weeks in, Amy noticed she liked the data side more. She decided to see where it led.

What it led to was a performance problem nobody had solved. The reports she was working on were slow because the database underneath them was designed badly. Her job, technically, was not to fix this. But she taught herself data engineering anyway, figured out the architecture, and fixed it.

She also went back to school for an MBA during the same stretch, while working full-time. While also raising kids. The goal here was: she wanted to get to executive level, and she was going to build toward it deliberately.

I still don’t know how one person can do all of this at the same time.

After almost eight years, she took what she describes as a calculated risk and joined a company in a completely different industry, different tools, different everything. She was the first permanent data person they’d ever hired.

She walked in on her first day and got pulled into a crisis meeting before she’d even set up her desk.

Well-oiled Machines

The company had just gone live with a whole set of new systems. Things were not working. Nobody handed her an onboarding plan. They handed her a problem.

And I think this is actually a love language for some people. You know who you are.

She triaged. Put fixes in place so the business could keep making decisions in the short term. Then started looking at the underlying architecture. Then built a team slowly, hiring people who were curious and willing, including a couple of people from other departments who’d always been interested in data and just needed someone to take a chance on them.

I asked her what her proudest moment from that job was.

She said it was the day the team told her she didn’t need to be in a particular meeting anymore. They had it. She could step back.

“We were like a well-oiled machine,” she says.

Here is the thing about that. A lot of people would hear “you don’t need to be here” and feel redundant. Amy heard it and felt like she’d done her job. The point was never to be indispensable. The point was to build something that could run without her, and she’d done that.

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COVID Changed The Math

She had been aiming at executive level for years. Had her reasons and her plan. And then COVID happened, and she was home, truly present with her kids, and she did what Amy does. She did the math.

The executive track means more of everything. More hours, more travel, more of yourself going to the company. And she realised she didn’t actually want to give that. Not because she couldn’t. Because the whole reason she’d wanted the executive salary was to give her family a good life, and her family was right there needing something a salary couldn’t provide.

She let the executive ambition go. And started paying attention to what she genuinely looked forward to at work. The answer was consistent, and it had nothing to do with the technical side of the role she was in at that time. It was always the people. Mentoring someone, watching a person figure something out, grow into a role, go somewhere new because she helped them get there.

She kept that information.

Analyse, Conquer, Evolve

There were more layoffs after that. Four total across her whole career if I counted that right. The 2009 one was the hardest, the one that required the most from her. Each one after, she was more ready. More practised. The armour went on faster.

After two layoffs in quick succession, barely a year apart at different companies, she sat down with her husband and said, “I think it’s time.”

She had been thinking about career coaching for a while. She knew she needed experience behind her first. Knew she’d have to build a reputation slowly. But after two layoffs in a row and zero motivation to send out another corporate application, the timing stopped feeling like something to wait on.

They went through the finances, talked things through. The conclusion was to start now.

The business is called Analyse, Conquer, Evolve. The name is also the whole philosophy. You start by analysing where you are, which is different from where you think you are. Then you conquer what’s in the way. And then you evolve. The path changes, you change, and the destination you had in your head stops being the destination.

She told me that in high school, she was absolutely going to design motorcycles at Harley Davidson. There was no version of this story when she was in high school. Choosing what you want to do at 17 and sticking to it when it does not align anymore is a good enough sign to pick another path, and Amy’s story proves that multiple times, through the school switches, through the layoffs and everything else that came along with it.

“Change is good,” she said. “Because that’s where the evolution comes from.”

Thank you for reading! If this resonated, share it with someone who’s figuring it out too :)

The Messaging

Nina Ajnira Karisik was born in Bosnia and Herzegovina during a war.

She grew up in a country that was still putting itself back together. The adults around her had been through enough that dreaming felt like a luxury they couldn’t even afford to encourage. What they did encourage was keeping heads down, being “realistic” and not being “silly” for dreaming.

And then, layered on top of that, the messaging that a lot of girls her age got, regardless of where they grew up: logic is for boys. Arts and writing are more suited for girls.

“You’re so girly, so fashionable, so Hilary Duff. You can’t do programming.”

The thing is, Nina was already coding at home. She was designing her own websites, running user tests, doing browser testing, and she liked it very much. It felt natural to her.

But the messaging was so loud and so consistent that when she got to university, she studied visual arts and communication design. Not because she loved it but because it felt like the safer version of herself to believe in.

“I was not even a good designer,” she told me, laughing. “I was more of a person who codes the thing and thinks about how it functions and looks at the usability. But I chose design because that’s what felt comfortable.”

I get the feeling that this is relatable for a lot of people. Doing a version of the thing they actually want to do, just slightly to the left of it, because that felt like the acceptable option.

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Starting From Scratch

When Nina moved to Melbourne, her qualifications didn’t follow her. The degree, the work she’d done, the experience she’d built — none of it transferred as she had expected. She had to start from scratch.

Her first job in Australia was as a fundraiser. Nina was standing in a shopping centre and asking strangers to donate to a charity.

She was good at it. It was a way for her to unpack the conditioning and prove to herself that she can do what she sets out to do.

She moved into a call centre after that. Social media messaging, customer service, and health insurance queries, among other things. She would get on a call with someone who needed help, and she could hear exactly what the problem was, but she could not fix it, because it was out of her hands. She wanted more control. She wanted to be the one who could solve it.

She didn’t yet know that this feeling had a name, or that it pointed somewhere specific.

The Workshop

She was 25 or 26 when she walked into a one-day programming workshop in Melbourne. Not a course level commitment. It was just a day.

She sat down. They started working through things when something clicked.

“I realised, oh, I am this kind of person. This is a community I could see myself in.”

And just like most of us, she already saw all the problems with the idea before she even let herself consider the possibility. She wasn’t a permanent resident yet. She couldn’t enrol in a four-year degree without citizenship, and even then, the cost was enormous. She did the mental math, and it didn’t work.

“That devastated me,” she said.

Within a year she found a different path. A six-month programming course, nights and weekends, alongside her full-time call centre job. Up at 7 am to code before work. Weekdays and Saturdays in class.

She questioned herself the entire time. Coming from an education system that didn’t encourage questions, asking for help felt almost physically difficult to her. The doubt wasn’t just about whether she was good enough. It was about whether she was even allowed to be there.

“If you are told something for 25 years,” she said, “that is going to be very scary to go against. But the feelings are valid. And people are very happy to help. If that person is not happy to help, that’s their problem, not yours.”

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Don’t Let the Lists Control You

It took five years before she felt genuinely good at it.

Not five years of smooth progress. Five years of pushing, questioning, and sleeping badly because she was trying to wake up at 5 am to code four hours before work and only getting five or six hours of sleep, which made her less sharp, which made the coding harder, which made the whole thing feel impossible.

The time management problem took five years to solve too. She learnt, slowly, that the to-do list was something she controlled, not the other way around. The tasks could move to the next day. She was allowed to go to sleep.

“I controlled the list,” she said. “The list doesn’t control me.”

She said it like it was obvious. It is not obvious. It took her five years to get there.

The community she built around herself helped. She found other people who were in the same situation, maybe one step ahead, and watching them made the whole thing feel real.

She mentors a lot of people now. She shows up for them because people showed up for her.

Pretty

She is a software engineer now with a full-time job, no alarm clock, cats fed by 7 am, and startup work before and after.

The startup is called MadeApt. The idea came from the same frustration she felt in the call centre, being on the phone with someone who has a real problem and not being able to do anything about it. MadeApt connects customers with global tailors for custom-made clothing. She mapped the whole process manually first, matching customers with tailors, sourcing fabric, coordinating fittings, doing every step herself. Then she coded it. Then she built agentic workflows, so it runs without her having to touch every piece.

She gave a talk recently where she said, offhand, “Wouldn’t it be cool if this happened?” About a feature. Then had to go home and actually build it.

“It was really difficult,” she said. “But then it’s so pretty now.”

I liked that she used the word pretty.

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Why Are You So Special?

She told me something toward the end of our call that I think needs to be drilled into all our heads somehow.

I asked what she would tell her younger self, at the moment she was most scared.

She said, “Look at the things you’ve already done that you’re proud of. Those things happened because you willed them to happen. So why do you think you can’t do it again? Why are you so special that you get to be the one person who can’t repeat their own success?”

It landed a bit differently than I expected. Most people frame this answer as reassurance. She framed it almost as a challenge. You’ve done hard things. You’re not exempt from doing more of them.

Perfect. That’ll do it.

She also said something about AI. The job market is scary right now. The messaging is loud. People are being told they’re not needed, which is a version of the same message she got as a girl about programming. And her response to it is the same as it was then: go to meetups. Talk to people. Build things, even if they’re bad. Something that feels obvious to you might be exactly what someone else will pay for.

“Just go step by step,” she said. “Be kind to everyone around you. If they’re not kind to you, that’s their problem. Build things that make you joyful, even if they’re really bad. That just means you have good taste and you know it should be better.”

I love the way she phrases these lines; I never saw it coming.

She grew up in a post-war country where the adults had stopped believing in big things because big things had hurt them. She moved to Australia with credentials that didn’t count. She was told, more than once and in more than one language, that programming was not for people like her.

She’s a software engineer with a startup and a community.

The messaging was wrong. It just took a while to prove it.

Thank you for reading! If this resonated, share it with someone who’s figuring it out too :)

Especially with someone who’s been sitting on an idea they’ve been told isn’t for them. It might be exactly for them.

Vannessa Haydeé Weber grew up believing in a version of success that most of us believe. Go to school, then get a respected job, work hard, and build something stable. That was the whole plan, and for a long time, she followed it exactly.

She has three degrees. None of them wasted. None of them was the plan either, not by the time she finished the next one.

A BA in Broadcast Journalism with a minor in Public Relations, because she loved the program but quickly learned she didn’t love the industry. So she quietly pivoted into higher education admissions.

An MBA, picked up while already working in admissions. A few years later, she moved to a different university into their Military and Veteran Education Benefits office, starting as a School Certifying Official and eventually growing the role so significantly that two new positions were created around her, Assistant Director, then Associate Director. She was recognised twice by her field’s professional association for her contributions. This is where she became, not quite by accident, a real expert in VA and DOD education benefits. One of those job titles that sounds invented until you spend ten minutes talking to her and realise it’s an entire universe of acronyms that real people’s lives depend on.

(Quick translation, because I needed one too: VA is Veterans Affairs, the US government department that supports military veterans. DOD is the Department of Defence. The GI Bill pays for veterans’ education. VR&E helps veterans with service-related disabilities find careers. Vannessa is fluent in all of it now.)

And an MS in Research Psychology and Data Analysis, finished in 2019, with a thesis that was showcased in the ASP conference in Washington DC. This one she actually thought would keep her in academia for good, a landing point, not another sideways step.

It didn’t. Not because anything went wrong but because something kept catching her attention, over and over, inside the work itself.

Sorry, I just had to title it like that, couldn’t unsee it once I saw it.

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The Gap Nobody Was Filling

Big organisations, the Microsofts and Amazons of the world, can pay for excellent research and evaluation support. They have the budget. Smaller organisations, especially community-based and minority-led ones doing genuinely important work, often can’t.

She gave me an example. A nonprofit in Central Florida – They’ve known for years they needed proper impact measurement, someone to collect real data and tell them honestly whether they were actually helping the community the way they thought they were. But the firms that do that kind of work are chasing multi-million dollar contracts. A small nonprofit isn’t on their radar.

“It’s not that these organisations don’t know they need the service,” she told me. “Once they realise they need it, it almost becomes a moot point, because they can’t afford it anyway.”

Three degrees in, this was the gap she’d been circling without naming it. Research she was trained for on one side and people who needed it and couldn’t get it on the other, no bridge in between.

A Glass of Wine in San Francisco

The pivot that became her business didn’t feel like a pivot while it was happening. It felt like a glass of wine in San Francisco.

She and her husband had gone to the Bay Area for a slightly different reason. Her husband is a big Clint Eastwood fan, and Eastwood owns a bed and breakfast in the area. They went hoping he’d be there. He was not. They had a lovely day anyway.

On a whim, they pulled over at a small wine bar they spotted while driving. A few glasses in, Vannessa found herself talking more freely than usual about something she’d love to build one day. The kind of sentence that usually trails off into “but...”

Her husband just stopped her.

“Why not?”

She started listing the excuses like, “I’ve never run a business before”, “it’s too risky”, “where would I even start”, “would I even get clients”.

He didn’t argue with the excuses. He just walked her through them, gently.

“Think about every business that exists right now, from Coca-Cola to the small shop down the street. At some point, every single one of them had never started a business either. And then one day they did.”

“It began to feel like something I could do,” she said, “if I just broke it into smaller steps.”

Drunk words are sometimes sober thoughts, I told her. She agreed the tasting really helped.

What’s interesting is that this wasn’t really separate from the first three pivots. It was what they’d been quietly building toward. The communications instincts. The expertise. The research training. None of it got left behind when she started the company. All of it got folded in.

“Best of all,” she told me, “I make use of my three degrees daily, just in a different way than I originally envisioned.”

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The Bonus Becomes the Whole Paycheck

She kept her full-time job for about a year while building the company on the side, the way you’d expect from someone whose whole life had trained her to be careful about leaps. Then in January 2025, she made the call. Left full-time employment entirely.

Exciting. And then, almost immediately, terrifying.

“Up until that point, that income was what was paying the bills,” she said. “The money from my business, it was kind of extra. A little bonus. All of a sudden, all I had was the bonus.”

The hardest stretch was around March of that year. The savings cushion was thinning. Her husband was still employed, fully supportive, but it genuinely took both of their incomes to cover everything. She remembers lying awake some nights doing the math, having the kind of conversations with him about whether he could pick up overtime.

“I don’t want to sugarcoat it,” she said. “It was emotionally taxing.”

What got her through wasn’t a dramatic turnaround. No marketing budget, no billboards, just her time and a reliable car. Local networking events, free or easily accessible, mostly in person.

I asked her what advice she’d give about networking, because the way she answered it told me something about who she is.

She said she’s an introvert. Rooms full of people for long stretches genuinely drain her. So her answer was not to push it, but it was: be picky. You don’t have to go to every event, which was a mistake she made when she started. Narrow it down by cost, by relevance, by whether the room is full of people you want to talk to.

And then, once you’re there, stop performing.

“I’m just there to meet people,” she said. “If I get a client out of it, that’s a bonus. I don’t have to put on an act. I can just be myself, and that will be good enough for a lot of people, and it won’t be good enough for some people, and that’s okay.”

She told me about a networking event a month and a half before our call. Sixty-something women in the room. She spent the entire hour and a half at one table with three other women. Didn’t rotate. Didn’t network the way you’re supposedly meant to.

None of those three women has become a client. None of them probably ever will. But they text now, a genuine relationship. When something comes up, when a client interaction goes sideways, when she just needs someone who gets it.

“It doesn’t matter how many people are in the room,” she said. “What matters is who gravitates toward you by you being yourself, and who you gravitate toward by them being themselves.”

I am, for the record, fully on board with adopting this as a personal philosophy.

Confidence Comes After, Not Before

I asked her about confidence, specifically how she built it, since “believe in yourself” is the kind of advice that means nothing until someone tells you what it looked like in practice.

The wine bar spark was real, she said, but the spark itself didn’t accomplish anything. What actually built her confidence was watching the tangible things pile up. Articles of incorporation. A federal tax ID number. Small, boring, bureaucratic proof that this was really happening.

“It was no longer the spark of I could do this,” she said. “It was the confidence that I am doing this.”

This is, in a way, the throughline of all four pivots. None of them happened because she suddenly felt ready. She wasn’t ready for admissions work when she went into it. She wasn’t ready for VA benefits expertise. She wasn’t sure research in psychology would lead anywhere different. The readiness, every time, came from doing the next small thing and noticing she was still standing afterwards.

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What she wants you to know

She told me about the people closest to her not fully understanding what she does. Not her parents, who came to the US from Latin America chasing the American dream and hoped she’d follow a familiar shape of it. Friends. Cousins. People who love her but don’t know what to ask about regression analysis or impact evaluation, so it can feel, in the moment, like they don’t care.

She’s come to believe that’s not what’s happening. They have their own lives. Her business matters enormously to her, but it doesn’t have to matter equally to everyone she loves for their support to be real.

“It comes from a good place,” she said. “It just doesn’t always feel good in the moment.”

I told her about a conversation I’d had with my own dad, who once asked me what I was going to get out of this newsletter. I told him I just wanted to do it. Wasn’t that enough?

She didn’t try to fix that for me. She just said she bet my dad was hoping it would go well for me anyway, even if he didn’t fully get the why.

Vannessa’s pivot doesn’t have a single dramatic before-and-after photo. It has three degrees that each looked, at the time, like the responsible next step rather than a departure from anything. And then a glass of wine, and a loving husband, who finally gave her permission to notice what all three had been pointing at the whole time.

“Careers are far less linear than we’re taught to believe,” she told me. “Most people are improvising more than they admit.”

She’d know. She’s been improvising, carefully and thoroughly, the entire way.

Thank you for reading! If this resonated, share it with someone who’s figuring it out too :)

Seven issues in, that is not the pattern.

Nobody felt ready at any age.

Not Maggie, who was moved into analytics by her VP during a reorganisation and questioned the decision the entire time it was happening, even after it had already happened to her. Not Amanda, who spent a year deliberately building a financial cushion specifically because she knew she wouldn’t feel ready; she just needed enough breathing room not to panic. Not Dr Hari, who stepped out of it because circumstances forced his hand each time. Monet, who just went for it anyway, not because she could see the path forward, but because she wanted to.

If you are waiting to feel ready before you do the thing, every single person I’ve spoken to would tell you that’s backwards. Readiness seems to be a byproduct of action, not a precondition for it.

Almost nobody’s first move was the right one.

Ana went from architecture into management before eventually building her own thing. Monet had ten jobs, not one pivot. Dr Hari went from Ayurveda to medical transcription to insurance before landing anywhere close to where he started.

The sideways step isn’t a delay before the real path starts. It tends to be a structural part of the real path. Every one of these people used the “wrong” move later, sometimes years later, in ways they couldn’t have predicted at the time.

No leaps are sudden.

Every pivot in this newsletter looks sudden from the outside. She quit her corporate job. He left Silicon Valley. She walked away from architecture. But sit with any of these people for an hour, and the sudden part disappears completely.

Maggie's VP didn't wake up one day and move her into analytics; it followed years of Maggie quietly digging into marketing data nobody asked her to touch. Amanda didn't leave engineering on a whim; she spent a full year building a financial cushion first, specifically so the leap wouldn't feel like one.

Even the leaps that look instant, a single conversation, a single workshop, turn out to be the visible tip of something that had been moving underneath for a long time. What looks like a jump is usually just the moment the rest of us finally notice.

What I think this means.

The zigzag isn’t a detour from a real path that’s happening somewhere else. The sideways steps, the jobs that didn’t fit, the degrees that seemed unrelated, the years of feeling behind, all of it appears to function as the actual mechanism by which people end up somewhere they belong or atleast, want to be.

I’ll keep tracking this as more issues come out. So far, seven for seven.

Thank you for reading! If this resonated, share it with someone who’s figuring it out too :)

Her very first CS class at college ended that plan in about a semester. It was a weed-out course, and well, it weeded her out.

So, she did what seemed logical at the time: she went in the opposite direction. Communications. PR. Something glamorous and nothing like code.

Her dream was to do PR for a non-profit arts organisation. A symphony, a ballet company, but she got a job promoting accounting conferences.

I would have also reconsidered my choices at that point.

Her second job was better. Hospital and healthcare communications, good boss, real work, media relations, internal comms and digital marketing. She was handling data alongside everything else and had nobody to teach her what to do with it. So, she started digging in on her own, all out of curiosity and no plan behind it.

“I didn’t think it could lead to a career change,” she told me. “After all, my major was Communication.”

The Call She Didn’t Make

Here’s the thing about Maggie’s story. The pivot didn’t happen the way you’d imagine pivots are supposed to happen in these stories. There was no breaking point. No quiet moment of clarity in the early hours. No dramatic resignation.

Her VP just walked up to her one day and told her she was doing analytics now.

Her previous role had been split between two other people during a team reorganisation. The work she’d been doing no longer existed as a job. Her boss laid it out simply, “This is your job now. We don’t have another job for you; your alternative is to not have a job.”

“I had bills,” Maggie said. “So, I was like, okay, I want a job. Let’s see how it goes.”

She questioned it even as it was happening. She’d spent years doing soul searching about her career, knew she didn’t want to stay in marketing, but still hadn’t figured out what she really wanted. Her first fear wasn’t “am I going to fail?” It was “Am I even going to like this?”

Her second concern was whether they would adjust her salary upward. Her boss told her, “You’re very green, you have no experience in this field, what you were making in marketing is more than adequate for basically an entry-level junior data analyst role.”

She took the job.

Lucky her, she loved it.

“The universe knew me better than I knew myself,” she said. “Because, despite my hesitations, I loved it. I am now thriving in this field so much more than I ever did in marketing.”

Her VP saw something in her before she saw it in herself.

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Screaming Into Pillows

By the time Maggie was 34, she was working properly in analytics. By 36, she was balancing a downtown Chicago office job with evening classes for her Data Science MS, grabbing dinner on the fly.

Monday to Friday, nine to five at her desk. Then, class for three hours or studying every other evening until bedtime. Then the weekends are almost entirely spent on homework and projects. She gave up her hobbies. She turned down plans with friends. She did this for four years.

“There were tears. There were screams into pillows. There was a lot of self-doubt.”

What kept her going was perfectionism.

I had not expected that answer. It caught me off guard, partly because I hadn't seen it coming, and partly because I could relate to it completely. I had just never connected those dots myself.

Her mum’s voice in her head: anything worth doing is worth doing well.

She was also spending her own money on top of the tuition assistance her company covered, and she was not going to waste it.

Her husband, watching all this, decided he wanted to get his master’s degree as well. He’d started years before and never finished. He enrolled, too. They ended up in their separate corners of the apartment, both studying, nobody annoyed at the other, both losing their minds in solidarity. When the breaks came around, they were both ecstatic.

Then COVID happened, and suddenly, having no social life was just normal.

Possibly the best timeline for a graduate degree ngl.

She was also older than almost everyone in her programme. Most of her classmates were in their mid-to-late twenties. She was 36 going in, 39 when she finished.

“I was able to connect what I was learning to the business problems I’d be solving,” she said. “Everything felt more tangible. I think if I were a student without any experience, it would have all been very abstract.”

She graduated with distinction. She got an A minus. Her GPA was 3.97. She told me she could still technically say she got straight As.

Perfectionism shining through

The Voice That Stays

Ten years into analytics, Maggie still has moments where she doesn’t think she’s good enough.

She’s worked through what to do with that voice. Nobody knows everything, but everyone knows something. The best teams are the ones where different people fill different gaps. Her background in marketing, the thing she spent years calling wasted time, turned out to be exactly what made her hireable for the job she’s in now. When she interviewed for her current role as a Data Scientist at a B2B tech company, they told her, “We really like that you have a prior career in marketing.”

She is 10 years older than some of her colleagues. Closer in age to her VP than to most of her peers. If she had stayed in marketing, she might be a director by now.

“But I know I’d be miserable. I was miserable in marketing fifteen years ago.”

The imposter syndrome comes back. She’s made a kind of peace with it.

Her old VP had a line she still thinks about: “You have to get comfortable being uncomfortable.”

Maggie took it to heart. When her current boss told her she really should learn to use the terminal, she felt the familiar dread, read a few articles, and then just learned it. It wasn’t as bad as she thought.

That’s usually how it goes.

So What If You Fail?

The night before she started her master’s programme, she was out to dinner with a friend from her old marketing team. She couldn’t stop thinking about that first CS class. The one that weeded her out of computer science all those years ago. What was she doing? What if she failed? Graduate school in data science requires programming and advanced math. The exact things that had beaten her once before.

Her friend looked at her and said, “So what if you fail? What’s the worst that could happen?”

“I was like, oh. You’re right.”

She already had the analytics job. She could retake a course if she needed to. Failing would not undo what she’d already built. Her sister-in-law chimed in to mention she’d had to retake something in her own master’s programme, and nobody knew, nobody cared, she still got the degree. The sky did not come down and put a big F on her forehead.

3.97 and just one A-

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Forty Years

One thing Maggie keeps coming back to when people ask about career pivots:

“We don’t realise how long our careers actually are.”

When you’re in college, you think, “I’ve already invested four years in this degree; I have to get a job in this field.” You graduate, and you have forty years until you retire. Forty. You have already spent double that amount of time on Earth by then, and you haven’t lived most of it yet.

She’s spent 12 years in marketing, 10 in analytics. She could switch today and still have twenty-something years left. Two more pivots, probably, if she wanted them. And she’s not scared of that.

“If AI takes my job in data science,” she said, “I could pivot again. I’m not scared to do it. I’ve got multiple different career paths I have experience in.”

Her ideal career didn’t even exist when she graduated. Data Scientist wasn’t a common job title in 2000. It wasn’t on anyone’s radar. She couldn’t have planned for it.

“Your ideal career might not exist yet,” she said. “You have 40 years. You have plenty of time for multiple twists and turns.”

When her VP moved her into analytics without asking, Maggie questioned it out loud, even as she was walking through the door. The universe made the call before she did. She caught up eventually.

The weed-out course didn’t end her relationship with code. It just delayed it by twenty years, took a long detour through accounting conferences and hospital comms, and dropped her off somewhere she truly belongs.

The zigzag was doing its thing the whole time. She just couldn’t see it from the inside.

Thank you for reading! If this resonated, share it with someone who’s figuring it out too :)

I scheduled this call early, at 6 am her time.

I don’t fully know what I was expecting. Probably someone half-awake? Giving me short answers, getting through it. Instead, Monet showed up to that call the way I imagine she shows up to everything. Completely present, thinking out loud. Saying things that made me think of self-awareness and career planning, and here I was, fumbling at 6 pm my time.

By the end of the call, I had that specific feeling you get when you’ve just spoken to someone who is several steps ahead of you in understanding themselves. Not in a way that makes you feel behind, but in a way that makes you want to go home and sit with your own thoughts for a while.

This is her story. It’s a different kind of zigzag: less dramatic pivots, more a slow, deliberate architecture of a life she truly wanted to live.

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Pivot #1: When the plan stopped making sense

Monet started university planning to go to law school. She was doing her BA in Psychology at that time.

She started noticing a common trend in her classes. They’d spend weeks learning a concept and then get told, “Actually, we don’t think that anymore.” She was being tested on information that had already been replaced, and that was frustrating.

But more than that, she started looking at the actual life of a lawyer. The hours, the pace, what it would demand from her. Her frustration with Psychology had also reached its limit, so she quit university at 21 and started working, and her parents thought she was crazy.

She wanted to be a mum. She wanted to work from home. She wanted her work to revolve around her life and not the other way around. A lawyer’s life wasn’t going to give her that.

Eventually, she picked up an administration role at a consulting company that worked in HR, career transition, and recruitment. Great on paper. But this is where things start getting interesting.

A colleague went on maternity leave. Monet took over her bookkeeping, which she enjoyed. When the colleague came back, the bookkeeping went back to her, and Monet was suddenly bored with nothing to do.

She told the partner she worked with. The partner introduced her to the accounting firm one floor above.

She started an accounting certificate course and a job upstairs the same week. The partner there had ideas about reimagining the entire accounting workflow, incorporating offshore staff, and rebuilding the process from scratch. Monet loved it. They broke everything apart and figured out how to put it back together differently.

Then the firm’s partnership split. Each partner started their own entity. Monet became Operations Manager at the age of 25, for their portion, a much higher role than her experience warranted.

“I felt like I’d done everything in a logical path that I was supposed to do. And I hated it.”

Pivot #2: The cooking diploma nobody expected

Here’s the thing about Monet you start to understand the more you hear from her. She doesn’t make decisions impulsively. She sits with them for a long time. But when she makes them, she makes them fully.

She had always loved cooking, but never pursued it seriously because the hours were brutal and the pay was worse. Cooks have to be there when everyone else is off work.

But at this point, she was done making sensible choices for their own sake.

“I decided I’m going to do something I want to do because I want to do it. Not because I can see the path forwards.”

She enrolled in a professional cooking diploma.

She was right about the hours and the pay. Line cooking was exhausting and poorly paid. But she said something about that period that I think needs to be mentioned.

“The learning was life-changing. Not because it had a purpose. Because it didn’t.”

Her final semester was also when she was pregnant with her first child.

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Pivot #3: Building something while everything else is moving

After her son was born, she and her husband started a consulting company. She was doing local bookkeeping and controllership work, found a full-time remote bookkeeping position with an online accounting firm, and stepped into her first startup environment.

She loved the initial culture. Everyone accountable, everyone invested. Small team, 20 people, all pulling in the same direction.

Then they grew to 50. The structures came in. The freedoms got restricted. Teams stopped talking to each other. The thing she had loved about it started to disappear.

She moved internally into special projects. Chaos, change and more planning, which she will tell you is very much her natural habitat. This was also the time she got pregnant with her second son. The company had treated her well, but something in how roles were being valued started to bother her.

On maternity leave, a colleague who’d started her own firm invited her to join as a business analyst. The vision was exciting: senior leadership, direct impact, the ability to shape things.

Then the team grew, and roles got added. Her access and influence got restricted. Same pattern, different company.

And then she had a medical emergency.

A ruptured ectopic pregnancy. Blood transfusions. Recovery that was longer and harder than anyone warned her it would be.

“When I came back to work, my brain and body were not the same.”

She described the specific thing she’d lost. She had always been able to see the interconnections between ideas. If A changes, then B, C, and D will also shift. After the ectopic pregnancy, in the initial recovery period, she could see A. She knew there were implications. But she couldn’t follow the chain.

She was trying to do work she’d always done, in a brain that wasn’t working the way it used to.

At the same time, the new HR lead at the firm and Monet were, her words, oil and water. After months of trying to hold things together, the thought of going into work made her cry.

“I couldn’t see a path to improvement. And I felt I was back in the same cycle.”

Another pivot?

Her husband had been the stay-at-home parent. He was ready to go back to work, and she was ready to stop, so they switched.

When her second son started pre-school, she started a computer programming degree with a specific goal in mind. She’d spent years in accounting and finance watching the same tedious tasks play out: e-commerce data being manually keyed into accounting software over and over again. She wanted to learn to build her own tools to fix that.

Then AI started gaining traction. The thing she was studying suddenly felt like it was moving in a direction she hadn’t planned for. This was her cue to stop and look around, which led her to notice something else.

She had colleagues who were underemployed or unemployed specifically because of their caregiving responsibilities. These were smart and skilled people who wanted to work but needed the flexibility to be present for their families. And the system wasn’t designed for them.

The more she thought about it, the less she wanted to go back to finance at all.

For the last several months, she’s been rebuilding the consulting company she started with her husband, this time around with a different vision. Courses, resources, tools. A podcast she launched on her own after collaborative attempts didn’t work out. A course called The Time Mosaic, which is about architecting your time, not just being productive. The question at the centre of it is: “Are you actually doing the things you care about, and if not, how do you make room for them?”

She’s also working on games. Simple ones, she said.

“Because we teach children that the best way to learn is through play, and then we completely forget that applies to adults, too.”

Okay, but why has nobody said this before?

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The 80% rule

I asked Monet about something she mentioned – Doing everything 80% and losing interest after.

I told her a lot of people would hear that and think, “She just can’t commit.”

She didn’t flinch.

She explained it like this. Some people love the 20% at the end. The refinement, the routine, the predictability of knowing exactly what’s coming. Those people thrive in recurring work. Monthly bookkeeping, processes that repeat, a rhythm they can count on.

Some people love the first 80%. Where there’s no structure yet, no order, everything is still being figured out, where you’re building the plan, not following one.

“That last 20% is when it starts to get predictable. You’ve done all the problem-solving. You know the core skills. What’s left is refinement. That part becomes routine.”

So, she finds the 80% mark, gets the project to a place where it can be cleanly handed over to someone who loves that last stretch, and moves on.

“I love project work. It’s got a start and a finish. You go in, get the mess cleared up, and the project ends at a logical handover point.”

I had genuinely never thought about work this way. The idea that understanding which part of a project energises you is the actual key to knowing what kind of work you should be doing.

The hike and the moment that changed things

At 25, Monet hit what she now calls her quarter-life crisis.

She’d wanted to be a young mum, but she was single. She’d wanted a family, not just a child. She was working an administration job she found boring. She grew up in a blended family full of tradespeople and entrepreneurs. It left her with a strange feeling: she could relate to almost anyone she met, but felt like she didn’t quite fit in anywhere herself.

She described herself as a chameleon, a wallflower. She could fit into any room, but nobody knew who she truly was, including, somewhere in there, herself, leading to depression and suicidal thoughts.

Her mum told her to make a list. Write down everything that would be involved in making a change. The act of planning and, within it, the act of control, Monet said, was enough to start shifting something.

“Things weren’t happening to me, I was in control, and the planning was a method to choose - what do I do next?”

Next, she went on a hike.

They came to a stopping point on the trail. A big rock overlooking a river. Trees, the sound of water, the feeling of being outside and fully in it.

“I want to be the person who experiences the outside. Not a city person who escapes to the forest one weekend.”

From there came a decision she’s been living by ever since. Stop being the chameleon. She found the things about herself that are non-negotiable, her values, her priorities, the shape of the life she wants, and built from those outward instead of fitting herself into whatever was already there.

So, self-awareness is key.

“That moment defined my career choices moving forward.”

What she would want you to know

I asked Monet at the end of our call if there was anything she wished I’d asked.

She said: I think what I’ve realised is that all these parts of my life look unrelated. But there’s a core that runs through all of them and holds the whole thing together.

She’s someone who lives first and then finds work that fits the life she wants. The bookkeeping wasn’t random. It’s a skill she can do remotely, which meant she could be home with her kids. The cooking wasn’t random. She loves food, she needs to eat, and it’s a skill that saves her money no matter what else happens. The programming degree wasn’t random. It was pointing toward the autonomy she was building toward.

“If you know what you want from life, and then you start making choices in reverse to support that, the choices don’t feel as big. Because they’re tied to one purpose.”

She also said something about learning that I wrote down immediately.

“Don’t think you’re going to go to school, and then you’re done. The world is constantly changing, and your position in it is always changing too. If you find joy in the learning process, it becomes a lot easier to adapt.”

This is also when I told her about the “floating thoughts” as I call them. The what-ifs of doing something else that never quite go away, even when you are working towards a goal you’ve planned out. I asked her if having them is a sign of doing something wrong.

Now I know the question to ask is simpler.

Is this moving me toward what I actually want? If yes, try it. If it’s not getting you further ahead than what you’re already working on, note it and keep going.

“Growth is not linear for almost anything. Look at a plant. It doesn’t just grow straight up. There are always offshoots, branches. Expect to slow down. Let yourself grow. And be willing to prune the things that don’t support where you’re going anymore.”

She never had one dramatic pivot. She had so many quieter ones. All of them look random from the outside. All of them, I now know, are pointing toward the same thing.

A life she doesn’t want to escape from.

She’s building it slowly, deliberately, in the gaps between school runs and podcast recordings and courses that didn’t exist last year.

6 am and all.

Thank you for reading! If this resonated, share it with someone who’s figuring it out too :)

He spent decades in tech, moving to Bay Area startups, crossing an ocean twice, fighting visa rejections, financial crashes, and corporate shutdowns. At the end, he realised most of his code was gone. He probably added some value to a company that was not his and that was about it.

So he went and planted a farm instead.

This is that story.

The beginning

Venky Talla graduated with an electronics and communication engineering degree in the late 1980s and walked straight into a rude shock.

“By ‘88, ‘89, software companies were starting to crop up everywhere,” he told me. “And they were looking for software engineers. But if you interviewed for a software company, they would say: You are not a computer science graduate.”

Electronics felt more hands-on when he chose it. He thought he’d make gadgets and things, and did not think about what would happen after graduation when the jobs simply weren’t there for someone with his degree.

He bounced around for a bit. Kept trying to break into software, same answer every time, “No.”

Then his manager, who was supposed to be keeping him in the company, did something he had absolutely no business doing.

He was flipping through a newspaper one day, looking for jobs abroad for himself, a habit apparently, and stumbled across a GIS technologist role in Doha, Qatar. GIS, or Geographic Information Systems, is the technology used to map and analyse geographic data, and it happened to be exactly what Venky Talla had been doing.

His manager called him over and pointed at the listing.

“But you’re my manager,” Venky Talla said. “You’re not supposed to be showing me job openings elsewhere.”

“Yeah, but you wanted to go to America, right?”

Venky Talla said yes. His manager said, “You can go halfway there.”

He didn’t even apply for it himself. His manager found his resume on a floppy disk sitting in his drawer, printed it out without asking, and sent it in. The next thing Venky Talla knew, he was being sent by first-class train to Chennai for an interview, and the interviewer didn’t ask a single question. Just: what’s your expectation, and when can you join?

“I said: Wow, this is cool.” He laughed, telling me this. If only interviews were so easy.

The father of the internet. In Qatar.

Doha in the early 1990s was a different world. Heavily censored. Magazines confiscated. Nothing coming in from the outside that wasn’t approved.

Then Venky Talla went to a conference in the US on a business visa and visited his friends who were doing their master’s degrees. They were all gathered around computers.

“I said: Where did you get all these images from?”

“It’s on the internet; you can download it.”

He bought a 14.4 kbps modem, and to give you a sense of scale, it would take roughly 90 minutes to download a single song today. He brought it back to Doha, Qatar, where there was no internet connection.

He was working for the telecommunications company there. He found a senior engineer who knew about the packet-switched network they were building, a system that routes data in small packets across a shared network, and asked him how to get on the internet.

The engineer didn’t know.

Venky Talla figured it out anyway. He contacted CompuServe, one of the first major internet service providers in the US, got them to configure a gateway through Rome, and dialled in.

“And next thing I know, I’m on the internet.”

Nobody knew this was even possible. Venky Talla just sat there in Doha, Qatar, connected to the entire world, completely uncensored, probably the only person in the country who was.

“Every time Al Gore says he is the father of the internet in the US,” he told me, grinning, “I claim myself as the father of the internet for Doha, Qatar.”

The visa fight and the letter

He wanted to do a master’s in computer science in the US. Proper CS. A real software degree, so nobody could tell him no again.

The US visa office told him no. Twice.

His Canadian boss found him furious one day and said, “Put all of that anger into a piece of paper. Just vent it. Give it to me, and I’ll proofread it.”

Venky Talla spewed, his word, venom onto the page. His boss, to nobody’s surprise, read it to say what Venky Talla already knew, “Dude, this is too harsh.”

His boss toned it down. The letter made the argument plainly: you gave me a business visa to attend a conference. I could have gone underground and stayed, like my friends suggested as a joke. I didn’t. I came back like a good citizen. Now I’m applying for a student visa, and you’re refusing. What exactly is the point of the system?

They gave him the visa.

He did his master’s and became a proper software engineer. He worked for Bay Area startups for years but moved back to India in 2003 to head up an India Development Centre, which is what companies used to call their Indian offices before they started calling them Global Capability Centres.

He was working hard. Really hard. Head down, building things.

And then Diwali 2008 arrived.

The gift

You guessed it, the 2008 financial crisis. It started in the US and spread everywhere fast.

Venky Talla, working in India, didn’t realise how bad it was getting.

“I didn’t even know there was a bloodbath going on in the US,” he said. “We were so hunkered down, working so hard.”

His CEO in the US decided to shut down the Indian operations to cut costs. They announced it on Diwali.

“So that was our Diwali gift.” I’d prefer no gifts, thanks!

He sat with that for a while, all that work, all that code, and when push came to shove, the company covered its own back and didn’t think twice.

That was the moment. Not dramatic, not a single epiphany. Just a quiet, bone-deep realisation that he was building something for someone else’s benefit and it wasn’t working for him anymore.

The farm that started as a hobby

Here’s the thing about the farm. It didn’t start in 2008. It started years earlier, almost by accident.

When Venky Talla was still in the US, some friends in India had pooled together to buy 30 acres of land for collective farming. They asked if he wanted in. He said sure, here’s the money, count me in. I don’t want to have to scout for land myself.

When he came back to India in 2003, he went to check on it.

“These guys were not doing anything. They basically gave up.” Thorny bushes everywhere. Completely unkempt. 30 acres of potential, abandoned.

He took his share of the land. Started going out on weekends with his kids. Planted trees. Tended to it slowly, treating it as a hobby while his day job paid the bills.

The land had no road. No electricity. No water. Not even good soil. He didn’t know what he didn’t know. He just kept showing up.

Then in 2006, a friend came with him to the farm one afternoon and plucked a guava off a tree. Wiped it on his pants and ate it.

By evening, he was throwing up. Not sure if this is going to stop me from eating freshly plucked guava the next time I visit a farm.

Venky Talla went back through the day in his head. They’d had the same lunch. The only difference was the guava. He called the caretaker.

“Did you spray anything?”

“Yes sir, last week I saw some bugs. I sprayed monocrotophos.” That’s a highly toxic pesticide, the kind that’s been banned in several countries now, including India, because of how dangerous it is to humans.

A one-week residue of a lethal pesticide had made a full-grown adult violently ill from a single piece of fruit.

“I thought: how much are we ingesting without even knowing? Because on a farm, I could pin down the cause. But what about everything else we eat every day?”

That was it. No chemicals. Period. Not organic in any formal sense, just: no synthetic chemicals on this land, ever again. He got desi cows, traditional Indian cattle breeds, and started using farmyard manure instead. Let things grow the way they were supposed to grow.

The night under the stars

The farm had no electricity for a long time. Venky Talla would go during the day and leave before dark. Too eerie, he said.

The caretaker kept telling him to stay overnight.

“I’ll stay when we get electricity,” Venky Talla said.

Eventually, the electricity came. Venky Talla got a tent, one with a mesh dome open to the sky, and pitched it in the middle of the farm.

He woke up in the middle of the night. Full moon earlier, but by 3am it had set, and there was nothing left but stars. Completely dark. Completely quiet. Except for the peacocks somewhere in the trees, calling out.

“I’ve lived in the city my whole life. The sky is always above us, but we never get to see the stars. It’s a humbling experience. I’m just this tiny thing on a planet that is itself a tiny dust particle in the cosmos. And we think we’re the centre of the universe.”

He was so vivid with the description. I could hear how those stars made him feel. The oxygen, the quiet, the absence of anything artificial. Something settled in him.

So he got more tents. Started having people come and stay. Let them sleep under the same sky, eat from the same land, wake up to the same peacocks, so he could share what he felt that night under the stars.

Young people loved it immediately. Families with parents were harder to convince. Not comfortable enough. So in 2015, he started thinking about building something more permanent. A farmhouse using repurposed wood and natural materials, designed to stay cool without air conditioning, built from the land itself.

He still hasn’t finished building his dream farm yet, a work in progress, but he never does not show up.

What it costs

His friends, pretty much all of them, thought he was out of his mind.

“What the hell are you doing, dude?”

His wife said she would support whatever made him happy. “I really got lucky with her”, he said, and I could hear how much it meant to him.

The money has been inconsistent. There were years after 2008 when he went back to software contracts for a couple of years at a time just to pay the bills and fund the farm. He did what he had to do.

“Right now, there is not enough money from the farm. That’s the idea I’m trying to make sustainable.”

But he’s not embarrassed about that. He talks about it the same way he talks about everything else, directly, without drama. It’s a problem he’s working on. He believes it’ll work out because the awareness is finally there. In 2008, he asked his friends if they’d pay more for organic produce, and they laughed at him. Now they message him asking if his mangoes are ready yet.

He was just early.

The thing he actually wants you to hear

I asked Venky Talla what he’d tell someone starting out now.

He said he tells his own kids the same thing he’d tell anyone.

Draw three columns. Label them: pastime, hobby, passion. Every week, write things you enjoy into the right column. Revisit it. Things will drop off. Some interests you had at 16 won’t matter at 22. But if something stays, consistently, in the passion column, that’s the thing.

He gave me an example of a friend who would party late and be totally exhausted, but if you called him at midnight and said, “ Let’s go fishing tomorrow at 5am, he’d be up, ready, at your door. That’s what passion feels like. You’re never too tired for it.

“80% of people are not happy with their jobs,” he said. “They’re making money, but they’re not happy. That’s a very sad way of living your life. A good chunk of your time is spent somewhere you don’t even like.”

He wanted to go into biology as a teenager. Loved life sciences. But he couldn’t stomach dissecting animals, so he switched to physics, maths, and chemistry instead, and ended up an engineer. He’s not bitter about it. But he thinks about it.

“My tendencies are all in life sciences. I was made into an engineer.”

Now he grows mangoes and guavas without chemicals on 10+ acres in Hyderabad, sleeps under the stars, feeds people food that doesn’t make them sick, and is slowly building something he hopes will show people that a simpler life can still be a full one.

“Even if I make a difference to 10 people. If I made a difference to those 10 people’s lives, that’s enough. I couldn’t do that writing software.”

I asked him what he’d tell his younger self at the hardest point.

He said, “Whatever has to happen will happen. And usually, whatever happens, it happens for your own good.”

Not a grand revelation. Not a strategy. Just a quiet acceptance that the zigzag has a logic to it, even when you can’t see it from inside it.

Venky Talla couldn’t see it when his visa got rejected twice. He couldn’t see it when Diwali 2008 arrived with a shutdown notice instead of a bonus. He couldn’t see it when his friends laughed at him for wanting to grow organic fruit. He saw it clearly under those millions of stars, and all it took was a night with a tent and the absolute love for nature he has.

Thank you for reading! If this resonated, share it with someone who’s figuring it out too :)

She was 31. Good job, great company, salary most people her age would kill for. She’d just finished one of those five-year career plans her firm asked everyone to fill out, and when she looked up from it, she realised she had basically built everything she’d written down.

And she felt completely hollow.

“I started looking at the people ahead of me,” she told me. “My bosses, the leadership, the people I was supposedly working toward becoming. And I realised there was nobody whose life I actually wanted.”

I didn’t say anything for a second when she said that. I think I just let it sit.

Because that’s the version of the story nobody talks about. Not the one where you hate your job, and it’s obvious you have to leave. The one where everything is working, on paper, and you’re still not okay.

How she got there

Amanda grew up watching her dad leave for work every morning as a civil engineer. He paid for her degree. He was, and still is, the person whose opinion she trusts most in the world.

She didn’t think too hard about the fact that she’d spent most of her childhood at tide pools. Or that she used to play The Sims for hours, not actually playing, just designing the houses.

Engineering made sense. Stable, smart, reliable. So that’s what she chose.

And she was good at it. Really good. That’s the part that makes this story more complicated than “she hated her job and left.” She didn’t hate it, not at first. The company kept giving her more, and she kept rising. Raises when she asked for them. Responsibility when she wanted it. A project she’d managed that started as a $15,000 feasibility study and grew into a million-dollar, 25-stakeholder monster she never quite felt ready for.

That project is where things started to unravel in her body before they unravelled in her head.

She wasn’t sleeping. She was losing hair. She was having panic attacks. She kept asking her team for support, and they kept telling her she was doing great. She kept losing sleep.

She was reading Your Money or Your Life around that time. The book asks you one question:

Heavy.

She read that, and all she could do was sit with it because it hit too close to home.

The trip that cracked something open

In 2018, a friend invited her to Honduras on a whim. Amanda got scuba certified. And something happened underwater that she’s still not quite able to explain fully.

“This is the coolest thing I’ve ever done,” she kept saying to anyone who would listen.

Being in the ocean, actually in it, seeing how it lives and breathes, she described it as meeting a version of herself that had been asleep for a long time. The tide pool kid, the one who never made it into the career plan.

A few months later, she went sailing in the Azores and met people living on boats full-time. Just moving through the world, unhurried, untethered. She came home and could not stop talking about it. Told her dad she wanted to do something like that someday.

He said, “Yeah, but you’re not going to give up your career to go do that.”

Then her mom got sick. She was gone, only a few years into retirement after decades of working a job she didn’t love and saving for a future she barely got to see.

Amanda and her dad started watching a YouTube sailing channel called Sailing SV Delos together to get through the grief. Young people moving through the world on a boat, making videos, just living. One night, after a few weeks of watching it together, her dad looked at her and said, “If this is something you want to do, you’ve got to go do it.”

“I don’t know if I would have left without his buy-in. I know that sounds strange. I’m an adult, I had the money, I could afford it. But he’s the person I’ve always used as a sounding board. And when he finally said yes, it felt like I gave myself permission.”

The amount of healing that can live in one sentence from a parent.

There’s something about losing a parent that rearranges the furniture in your head. Her mom had done everything right. Saved. Waited. Planned for later. And later didn’t come, not really.

Amanda wasn’t going to wait for later.

The exit plan

Here’s what she did not do: rage quit.

She gave herself a year. Taught herself personal finance from scratch, because she’d been contributing to a 401(k) without really understanding why or what it was even invested in. For those not in the US, a 401(k) is an employer-sponsored retirement savings plan that allows employees to invest a portion of their paycheck with valuable tax advantages and, often, an employer match.

She read the books. Opened brokerage accounts. Maxed out her retirement contributions. Moved back in with her dad when COVID hit, after giving up her apartment in LA, and saved almost everything she earned.

She made a profile on a crew-finding app for sailboats. Wrote out a list, almost a manifestation list, she said, of exactly what she wanted in a trip. Then a stranger messaged her out of nowhere: “We’re leaving from San Diego on November 1st to sail around the world. Want to come?”

She met him once. Decided he was probably not a serial killer. The next day, she had lunch with her boss and handed in her notice.

“Tim Ferriss has this line,” she said, “about how the stars are never going to align perfectly. There’s never going to be a right time to do the thing. You just have to go and figure it out along the way.”

The boss, whom she was most scared to tell, this larger-than-life personality who had invested years in her career, was thrilled for her. Everyone was. She walked out of that lunch feeling grateful and a little stunned.

“Real support isn’t just people cheering for decisions that benefit them. It’s people recognising when something is right for you, even if it means losing you.”

What two years on a boat actually looked like

She left San Diego. They sailed down the Baja California coast. Two nights in dark, rough conditions, the autopilot broke. Tools flew across the cabin floor. The boat pitched and rolled. Amanda had to hand-steer while the captain went below to fix it, and she had absolutely no frame of reference for whether any of this was normal or terrifying.

“I didn’t know what was dangerous versus what was just sailing. I was just trying to hold the wheel and not lose it.”

She grew accustomed to the lifestyle. She spent months in the Sea of Cortez watching humpback whales migrate through, then crossed the Pacific and reached Fiji. Anchored off islands that most people only ever see in a travel magazine, they flip through at the dentist.

“The first-time dolphins showed up at the bow, I thought: there is no version of my office life where I ever would have experienced this.” – reminds me of what Ana said in issue #003

Eventually, the person she’d been sailing with had to go back to work. She didn’t want to stop. She found another boat in Malaysia, attached to an underwater content channel, but that one needed more repairs than she’d signed up for. So she left, again, and found a conservation programme in Borneo. Sea turtles. Coral restoration. Diving every day for something that mattered.

That was the pivot she hadn’t seen coming. The one that changed everything.

The coral

Amanda wakes up now at a dive resort in Indonesia, surrounded by people who care about the same things she does.

Mornings: diving with guests, taking underwater photos, talking about reef ecosystems with anyone who wants to listen. Afternoons: at the coral nurseries.

Coral fragmentation, in case you haven’t come across it, is essentially controlled propagation. You take small pieces of healthy coral, grow them in underwater nurseries, and transplant them back onto damaged reefs. It’s painstaking, slow, careful work. It matters because coral reefs cover less than 1% of the ocean floor but support about 25% of all marine species. They are collapsing globally, and people like Amanda are literally underwater, by hand, trying to grow them back.

She also gives presentations to resort guests. Posts daily stories on Instagram, sending the underwater world through her phone screen into living rooms where kids are eating breakfast.

“Some of my friends have told me their kids watch my stories first thing in the morning. They’re obsessed with the fish, the coral, all of it. That makes me really happy. If I can make even one kid care about the ocean, that feels like something.”

Conservation work doesn’t pay her. She knew it wouldn’t when she chose it, and she chose it anyway, because the engineering years were never just about the career. They were about building enough of a foundation that one day she could do something that mattered without needing it to pay her back.

Could that be the answer??

The part that’s harder to talk about

When Amanda goes home to California, something shifts in her that she can’t quite explain and can’t quite shake.

Her friends are in their late 30s. Houses, partners, cars, nice things, the markers of a life assembled correctly. She visits them, and even though she doesn’t actually want what they have, she still feels the gap. Still catches herself doing the comparison.

“Sometimes I think I’m living this Peter Pan thing. Like, I’m just avoiding growing up. Even though I know that’s not what this is.”

In Indonesia, nobody tracks what she’s wearing. She doesn’t own much. She’s fine with that, most of the time. But she lands in California, puts on her skinny jeans, and her friend goes “Nobody wears skinny jeans anymore,” and suddenly she’s in a shop, wondering if she needs to buy white sneakers to feel like herself again.

“In Southeast Asia, I just exist. I don’t feel the pressure to fit in because I know I’m not going to. But the second I’m home, it comes back. The need to match. To look a certain way. To keep up.”

She said this almost reluctantly, like she wasn’t sure she should admit it. But I think that’s exactly why it’s worth saying. Living the unconventional life doesn’t mean the conventional pull disappears. It just means you get to notice it more clearly.

She doesn’t know what comes next. Maybe coral restoration for another few years. Maybe something she hasn’t thought of yet. She told me the biggest thing this whole journey has taught her is that she doesn’t need to know.

“The more I trust that things will work out, the more they do.”

What she wants you to take away

She gets messages constantly from young people who want to quit everything and go save the ocean. She’s honest with them: there is very little money in conservation, and what little exists should go to the people who live there, not to visitors who will eventually leave.

But that’s not the point she’s trying to make.

The point is the parachute.

“Build a financial cushion first. It doesn’t have to be huge. It just has to buy you enough breathing room to figure out what’s next without panicking. I don’t need coral restoration to pay me because I built the freedom not to need it to. That changes everything about how I can show up for it.”

She wishes she’d understood personal finance earlier. Not to get rich, not to retire at 40, just to have options. Because options, she said, are what freedom actually feels like.

“It’s not about making a lot of money. It’s about understanding how to use the money you make in a way that creates room for your future self.”

I think about that a lot. Building room. Not for the version of your future that looks good on paper. For the version that actually fits.

At the end of our call, I asked Amanda if she ever thinks about her mom when she’s out there, in the water, doing this thing she loves.

She went quiet for a second.

“I think she’d be excited. She spent so many years in a job she didn’t love, saving for a future she didn’t get to enjoy. She’d be happy to see me actually doing the thing. Not waiting.”

Amanda is 37, planting coral in the Coral Triangle, the most biodiverse marine region on earth, in the middle of the sea, and she’s happy. Not the version of happy that looks good on a five-year plan. The real kind.

She’s not waiting.

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I have spoken to a few people now for The ZigZag. Some are thoughtful. Some are honest. Some are funny. Ana was all three at once, at full volume, with zero filter, and I was grinning the entire time. At one point, I just stopped and told her that I loved her energy and it’s contagious. She laughed and said, she sometimes worries about it. Too much energy for a director, apparently.

That is the most Ana thing she could have said.

Portuguese, 40, with one of the most non-linear careers I’ve encountered: architect, controller, marketing manager, digital agency owner, content creator, business unit director, fractional CMO. She’s received a standing ovation in a boardroom, been called a unicorn by HR, and once quit a job to spend 75 days across six countries in Southeast Asia. She has eaten all the tropical fruit she could find there and still missed cheese.

She surfs now, and does a lot of other things, joyfully, which she says is exactly the point.

This is her story. It has several chapters, none of them planned, and every single one of them is load-bearing.

Age 25: The pivot that the financial crisis forced

Ana was the kind of student who, in third grade, turned down a trip to Malaysia with her parents because she needed to study. She told me this with the tone of someone confessing something mildly embarrassing. I told her I had never met anyone like that. She laughed because she knows.

She grew up wanting to be an architect. Not because someone pushed her, but because she genuinely loved everything about it. “There’s something about architecture that holds everything together. Drawing, history, mathematics, physics, construction, geography. It collapses the world into one discipline and asks you to make something beautiful and permanent out of it.”

She was all in.

She got into one of Portugal’s top architecture schools & graduated in 2010, straight into the financial crisis.

Almost no jobs. And the ones that did existed were people asking for attics that couldn’t physically exist, detailing bathrooms and whatnot, but all of it paid too little. She had studied urban planning, museums and sustainable architecture. She had no interest in bathroom details.

So, at 25, she enrolled in a master’s in management at one of Portugal’s top business schools, ranked among the top 20 in Europe. To everyone around her, it looked like an unlikely pivot. To her, it made sense.

“Architecture and management use the same underlying wiring. Both demand that you think in systems, work analytically, and find creative solutions within complex constraints. The subjects looked different on the surface. The mental framework was the same.”

“The materials changed. The framework stayed.”

That line follows her through everything that comes next.

The corporate years: The zigzag that was actually an education

What followed was anything but a clean climb. Communications. Controller. Trade marketing. Product manager. Marketing manager. Each move came not from a plan but from the world restructuring around her: companies reorganising, merging, shifting strategy. She worked at top global firms. At one point, she stepped out entirely and ran her own digital marketing agency.

Eventually, she returned to corporate, made director, and what emerged from all that movement was, as she put it, “a genuine, hard-won expertise in marketing and go-to-market strategy. On paper, it looked like a zigzag. In hindsight, it was an education.”

But here is the pattern I noticed. Every single company put her in the same situation: a blank page. A small division nobody knew what to do with. A broken function that needed fixing. A new market that needed building. Again and again, without her asking, she was handed the empty room and told to do her thing.

She traced it back to architecture school. You have a blank sheet of paper. What are we going to do with this? That question has followed her into every room she has ever worked in.

Accidentally becoming the person every company calls when they have no idea what to do is such a flex, don’t you think?

Age 36: The break, and the 75 days

36, working at a top fintech company, thriving, until everything that had held the role together fell apart at once.

“It wasn’t one thing. It was the slow suffocation of realising that the version of the job you signed up for no longer existed, and nobody was going to acknowledge that.”

At the same time, a relationship ended. Everything that had structured her life was shifting at once. That was also around the time she started surfing. When everything falls apart simultaneously, you find new anchors. The ocean became one of hers.

She knew something needed to change. So she quit.

“I broke. Not dramatically, quietly, from the inside.”

The financial hit was immediate, a full stop on the income. But what hit harder was the identity rupture. “You don’t realise how much of yourself you’ve outsourced to a job title until it’s gone and you’re standing there wondering who you are without it.”

And then, after a month or two of planning, she got on a plane. Singapore, Indonesia, Malaysia, Thailand, Cambodia, Vietnam. Six countries. 75 days. No deliverables, no performance reviews. Just her, a camera and places that had nothing in common with the life she had just stepped out of.

Bali was the turning point. She used the word cliché, knowing exactly what it sounded like. “But clichés exist because they keep being true. I didn’t come back with answers. I came back with a different relationship to the questions.”

By day 45, she was desperately craving cheese. Apples. Grapes. Cherries. The exotic thing had become the fruit she grew up with.

Moving through six countries so different from Europe, feeling compelled to document everything, she realised storytelling had always been her thing. The camera made it official. Combined with her marketing background, she came back as an agency owner too.

Quitting removed the golden handcuffs. The trip gave her a new perspective.

“Once you’ve seen how differently life can be lived, it’s very hard to unsee it.”

The people who questioned and the strangers who cheered

This is the part of Ana’s story I keep coming back to.

Throughout every pivot — the management degree at 25, quitting at 36, the 75-day trip, the director role that comes next — the people closest to her were the ones who struggled most to understand.

Nobody told her directly that she was making a mistake. But the questions were constant. When are you getting the next job? What’s the plan? How long are you going to do this?

“Those questions sound like concern but they feel like doubt. After a while, the difference stops mattering.”

Her family, her colleagues, and the people who had known her through the stable years had a framework for success. Her choices didn’t fit inside it. Her mother worried the way mothers worry and tried to talk her out of it more than once.

And then there were the strangers.

“People I met on the road, online, through the content. They didn’t question. They just cheered. No history, no agenda, just genuine support for someone doing something they found interesting. Sometimes that’s exactly what you need. Not wisdom. Just someone in your corner.”

Her best friend never wavered for a second. “That kind of belief, unconditional and no asterisks, is rarer than people think.”

There is something quietly painful about this dynamic that I think a lot of people reading this will recognise. The people who love you most are also the most invested in keeping you safe, in the version of safe they understand. The strangers have no stake in your choices, which makes their support feel uncomplicated in a way that family support rarely is.

She learned early to make peace with decisions that other people were not ready to understand yet. That is not a small skill. That is years of practice.

Age 39: The highest fall

This company had found Ana on LinkedIn. The HR director called her a unicorn: a rare hybrid of digital expertise, business school credentials, go-to-market depth, a traveller, and the ability to build from scratch. Nobody else had the combination.

She had an office. A team she loved and defended. A car she picked and customised. One and a half months in, she presented the entire company strategy to the board of directors, which she had worked days and nights to pull together earning her a standing ovation in the boardroom.

And then the same pattern emerged. Internal politics. She was going to go.

“By then, I was a director. I had a team, a salary that reflected years of climbing, and a level of professional credibility that takes a long time to build. Leaving that costs you in ways that are hard to explain to someone who hasn’t done it. Financially, it meant going back to zero income. Emotionally, it meant grieving something even when you know it wasn’t working. Socially, it meant watching people around you struggle to place you when you no longer had the title to do it for them.”

The relief was there again, but there was also something else. She liked that director title. She liked her team. She liked the car. Grieving something that was not working is still grieving.

Next came Japan and the Philippines. Knowing by then what travel did for her, she returned with a clarity she didn’t have when she left.

Where she is now

Ana is 40. Fractional marketing director. Content creator. Agency owner. An Airbnb project with her mother. Business ideas in various stages. And still, quietly, doing architecture for family and friends.

“It never really left. It just found its place.” – reminding me of what Dr Hari said in Issue #002

The travel is no longer stolen from real life. It is real life. Montenegro earlier this year. Australia is on the horizon. And when she is home, she is at the beach, doing a full meteorological study before she decides whether to surf, because that is exactly the kind of person she is.

Turned down a trip to Malaysia at age eight to study and now doing scientific analyses of wave conditions before going to the beach. Full circle.

“It started feeling right when the life and the work stopped being two separate things pulling against each other. Not every day is like that. But enough of them are. That’s when you know.”

The thing she wants you to know

“That the zigzag is not the detour. It IS the path.”

She spent years treating her non-linear choices as things she needed to explain or justify. the second master’s, the pivot into management, the content platform on the side, and the restlessness. She kept waiting to arrive at the version of herself that made sense as a straight line.

“What I know now is that every detour was load-bearing. The architecture training taught me how to think spatially and structurally. I use it every day, just not the way anyone expected. The management degree gave me the language to lead and scale. The years in corporate gave me the inside knowledge of how businesses actually break. None of it was wasted. It was all research.”

And this, which I am leaving exactly as she wrote it:

“Don’t optimise for safety at the expense of ownership. A salary is rented stability. What you build is yours. The scariest move I ever made was the one that finally put my name on something. That’s not a coincidence.”

She is designing a life the same way she was trained to design buildings. With intention, with structure, and with the understanding that the best spaces are the ones that feel inevitable once they exist.

One more thing she wants you to know, for anyone who is stuck in the overthinking: the clarity does not come before the move. It comes because of it. Waiting until it feels safe is its own kind of loss. Overthinking is not preparation. It is just fear with a to-do list.

Thank you for reading. If this resonated, share it with someone who’s figuring it out too :)

He worked 27 hours’ worth of work in a 24-hour day for five and a half years. Triple shifts. Different hospitals, each at least 10 to 12 kilometres apart, a bag of spare clothes always with him, sleeping once a week on Saturday night through Sunday afternoon. When I asked if it affected his health, he laughed and said he was healthier during that period than at any other time in his life.

I did not know what to do with that.

He wasn’t saying it to impress me. He said it the way you talk about something that just made sense at the time. Like it was just obvious. Like, of course that’s what you do when you love what you’re doing, and your family needs you, and life is moving fast, and you’re 24 and a little bit invincible. That laughing, unstoppable, figuring-it-out-as-he-went energy never left him. That’s what makes his story worth telling.

Where It Started And Almost Ended.

Dr Hari was a gold medallist. University topper across all four Ayurvedic colleges in his university, except that the institution couldn’t afford a gold medal, so they gave him silver instead. He told me this with a grin. He found it funny.

He had a plan: practice Ayurveda, stay true to what he trained for, and build something real. He opened his clinic. He was certain about it.

And then almost nobody came.

His patients wanted allopathic injections — conventional medicine. He said no. He was an Ayurvedic doctor, not an allopathic one, and that line meant something to him. One or two patients a week. Rent still due. A waiting room that just stayed quiet

This is the part that gets skipped in most career stories. The moment the plan doesn’t collapse dramatically. It just quietly stops working. No crisis. No epiphany. Just a slowly emptying waiting room and a realisation somewhere in the background that the first chapter wasn’t going the way he’d written it.

Pivot #1: The One Life Gave Him

In 2000, he saw a newspaper ad for something called medical transcription. Quick explainer: Medical transcription is converting audio recordings by doctors into written text. It can be their notes, diagnoses, or patient summaries. At the time, it was a booming industry, especially for processing records from hospitals in the US and UK.

It wasn’t what he’d imagined for himself. But it would pay the bills, and he figured he could do it from the clinic between patients. Easy enough, he thought.

It didn’t take him long to realise he was wrong. The screening process alone took six months with multiple rounds of testing, training, and on-the-job evaluation. He almost talked himself out of it halfway through. But he kept going, reminding himself: if you want to become successful, you have to survive first.

Once inside, his medical background changed everything. What his batchmates were learning from scratch, like the terminology, the clinical language, the ability to hear a complex word and immediately know what it meant, which he already knew. Out of 75 to 80 people in his cohort, he finished in the top three. He hadn’t even been trying that hard. He was too busy managing his other shifts. You know that one person who said, “I haven’t studied at all” and then topped the class? Yeah. That. Except – he actually didn’t, not for these exams at least.

Then he became a trainer completely by accident. A colleague was stuck on a medical textbook. Dr Hari stopped, explained it in two minutes. The colleague looked at him and said, “Why aren’t you teaching us?” Management heard about it. They asked him to train the whole batch. He said yes on one condition: “Cut my hours so I can keep my hospital shifts.”

He hadn’t planned to be a trainer. He hadn’t planned to be in transcription at all. But there he was, and he was good at it.

The Driving Force

There’s a part of this story that isn’t really about career. But it explains everything.
Dr Hari was the eldest son, and his father was a retired Indian Army officer. A good man, principled, not wealthy. When Dr Hari once asked him how the family was going to manage his sisters’ futures, his brother’s path, and his father’s answer was three words: “Tu Hai Na,” which in English translates to “You are there.”

That was it. Dr Hari picked those words up and carried them for the next decade.

He funded both his sisters’ weddings entirely on his own, which were grand, proper celebrations, the kind the family deserved. His father had no idea what it actually cost. He helped get his younger brother into a course, then a job, eventually all the way to the US. All of this while running between shifts, training batches of people, and figuring out his own next move at the same time.

And somehow — this is the part I genuinely cannot get over — he had a girlfriend through all of it. On his one day off each week, he took her to every cinema in the city. No compromise, he told me. She is his wife now. I was thinking, one day off a week, and he still showed up. Honestly, relationship goals

He said it with the satisfaction of someone who pulled off something impossible and knew exactly what he’d done.

When His Past Saved His Son

By 2007, Dr Hari was one of the most recognised names in his field. His company sent him to Bhutan to set up their first BPO system, where he spent six months, training the country’s first-ever batch of transcriptionists. A few years later, Colombo, for another six months. Two more batches. He had gone from a failing Ayurvedic clinic to training thousands of people across countries, without once sitting down to write a five-year plan.

Each step followed from the one before it. That was the whole strategy.

Then, in 2010, his younger son was born, and the story takes a turn I did not see coming at all.

His son arrived with serious complications. He had meconium staining, meaning he had passed stool before birth, which, when ingested, causes life-threatening complications. He also had signs of hyaline membrane disease, a condition where the lungs lack surfactant, the substance that keeps the air sacs from collapsing and makes breathing possible. It is most common in critically ill newborns and is genuinely a medical emergency.

Dr Hari had spent five years doing night shifts in a neonatal unit, i.e., a ward specifically for critically ill newborns. He knew exactly what he was looking at.

He knew that at 2 or 3 in the morning, secretions build up in a baby’s airway and need to be cleared, and that the window to do it is about ten minutes. He had inserted IV lines into over 200 newborns before. Thin catheters into veins as fine as a strand of hair, always on the first attempt. A skill usually reserved for postgraduate specialists. He had simply mastered it over years of night shifts, without ever realising how rare it actually was.

So, every night, he went and sat beside his son. Cleared his airway at 2am. He knew the timing. He had done it for other people’s children hundreds of times.

After seven days, his son made it.

The neonatologist, one of the most respected in the country, told Dr Hari afterwards that he’d had less than 50% confidence the baby would survive. He said Dr Hari’s presence through those nights was the reason his son was alive.

His son is 15 now. In his final years of school.

Dr Hari told me this part of the story with warmth, not weight. What came through wasn’t drama. It was a wonder how years spent in a neonatal ward with no connection to any career plan turned out to be exactly what his life needed him to know.

“There is a pre-filled path,” he said. “Only thing is, we fit into the grooves.

Pivot #2: The One That Came From A Hospital Bill

After his son recovered, Dr Hari filed an insurance claim. He got back far less than he had spent, which did not bother him, but it made him curious. How did this system actually work?

Call it luck, someone in the industry reached out. He joined a major private health insurer as a cashless processing doctor, a person responsible for approving or denying claims for hospitalised patients in real time. He started at the very bottom. Within a year, promoted. Then again. Then again. Twelve years later, he was Associate Vice President, having trained several hundred professionals and built an entire training and quality function along the way.

He hadn’t planned to be in insurance. He followed a hospital bill into a brand-new industry.

In 2022, it was comfort that pushed him out, not crisis. He described the end of that chapter like a government job. Steady, secure, no real challenges left for him considering the kind of person he was. And that bothered him far more than uncertainty ever had. He always wanted to find something new that challenged him.

He later joined a renowned health insurance company to build their in-house health claims team from scratch. Two years later, Vice President. The week we spoke, he had just been asked to expand his work to a new city. The conversation had happened two days before our call. He hadn’t even processed it yet.

He was just excited.

That’s the word. At every turn, after every pivot, the man was just excited about what came next.

The Thing He Never Let Go

Through all of it, the clinic, the transcription, Bhutan, Colombo, the insurance career, the vice presidency, Dr Hari never actually left medicine.

Medical transcription had medicine in it. Health insurance has medicine in it. His current role has medicine in it. He is even the designated point of contact from his company for AYUSH guidelines (the framework for traditional Indian medicine systems, including Ayurveda) under the Government of India. The gold medal he won and couldn’t receive is still part of who he is.

He still plans to open an Ayurvedic or Panchakarma centre one day. Ten years from now, maybe. He mentioned it almost in passing, like it was always assumed.

When I asked what he’d tell someone building a career, he didn’t give me a strategy.

“Don’t lose your fabric. Whatever you were built from, whatever the baseline is. Take the pivots, go where life sends you, but don’t abandon it completely. It keeps showing up. Let it.”

LIKE + LOVE = LIVE

He told me about something a neuroscientist once shared with him that he has never forgotten. Start with LIKE-ing your work, do it often, and you fall in LOVE with it. Once you are OK with this change in feeling, strike out the O in LOVE and K in LIKE, and what you are left with is LIVE. You live it. And when you live it, exhaustion stops being part of the equation.

I don’t think you can plan for that. But I think you recognise it when you stumble into it.

Dr Hari stumbled into a neonatal ward at midnight at 24 years old, and every pivot since has circled back to the same place. He didn’t plan the zigzag. He just kept showing up for it, with a spare pair of clothes in his bag and absolutely nowhere else he’d rather be.

Thank you for reading. If this resonated, share it with someone who’s figuring it out too :)

But here’s what kept pulling me back to actually do it: I’m in my twenties, I have a job, and I still find myself asking, “Am I really sure about any of this?” I don’t think I’m alone. We’re each handed an invisible script: study, get a good job, build a career, repeat, and somewhere along the way, most of us quietly wonder if we’re following the right one, or if there even is a right one.

The ZigZag is my attempt to answer that, one conversation at a time.

Here, I write about people who did not take the straight road. People who switched fields, started over, bet on something unlikely, and somehow landed exactly where they were supposed to be, doing work they actually love. Not because they had a five-year plan, but often because they didn’t.

This isn’t a hustle culture newsletter. It’s not career advice. It’s stories. Real ones, from real people, told honestly. The kind that makes you think, “Okay, maybe I don’t have to have it all figured out right now.” Because if there’s one thing I keep finding, the most interesting careers are rarely the ones that went in a straight line.

Welcome to The ZigZag. I’m glad you found your way here.

If this resonated, share it with someone who’s figuring it out too :)